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Chemical Structure| 84832-01-9 Chemical Structure| 84832-01-9

Structure of 84832-01-9

Chemical Structure| 84832-01-9

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CAS No.: 84832-01-9

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Product Details of [ 84832-01-9 ]

CAS No. :84832-01-9
Formula : C8H5F2NO4
M.W : 217.13
SMILES Code : O=C(OC)C1=C(F)C=CC([N+]([O-])=O)=C1F
MDL No. :MFCD07368850
InChI Key :CIHHBTMZOLRCRL-UHFFFAOYSA-N
Pubchem ID :43449035

Safety of [ 84832-01-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 84832-01-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 3
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 46.46
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

72.12 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.3
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.8
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.5
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.69
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.55

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.42
Solubility 0.829 mg/ml ; 0.00382 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.93
Solubility 0.253 mg/ml ; 0.00117 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.42
Solubility 0.825 mg/ml ; 0.0038 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.35 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.96

Application In Synthesis of [ 84832-01-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 84832-01-9 ]

[ 84832-01-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 84832-01-9 ]
  • [ 84832-02-0 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen;palladium 10% on activated carbon; In ethanol;Inert atmosphere; [00176] Step B: 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25 M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g, 99%). The material was taken directly onto the next step.
99% With hydrogen;palladium 10% on activated carbon; In ethanol; 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25 M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by thin layer chromatography ("TLC"), N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6- difluorobenzoate as an oil (15.66 g, 99%). The material was taken directly onto the next step.
99% With hydrogen;palladium 10% on activated carbon; In ethanol; Step B: 10% (wt) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by thin layer chromatography ("TLC"), N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6- difluorobenzoate as an oil (15.66 g, 99%). The material was taken directly onto the next step.
99% With hydrogen;palladium 10% on activated carbon; In ethanol;Inert atmosphere of nitrogen; 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25 M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The <n="68"/>mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g, 99%). The material was taken directly onto the next step.
98% With palladium on activated charcoal; hydrogen; In ethanol; at 20℃; General procedure: Pd/C (0.1 eq.) was added to a solution of the nitrobenzene (1.0 eq.) in EtOH (0.2 m). The suspension was degassed with H2and the reaction was stirred at room temperature upon complete consumption of the starting material. Then, the mixture was passed through a Celite pad and the filtrate was concentrated in vacuum. The product was used without any further purification.
98% With hydrogenchloride; iron; In ethanol; water; at 80℃; Alternatively: 75 (1 g, 4.6 mmol, 1.0 eq.) was suspended in abs.Ethanol (0,25 M) and aqueous HCl solution (1 M, 4.6 ml, 1.0 eq.) andheated to 80 C. Fe0 (282 mg, 5.1 mmol, 1.1 eq.) was added to themixture and stirred at 80 C until complete consumption of the starting material. The crudewas poured through a pad of Celite andthe filtrate dried in vacuo. The productwas obtained as a white solidand was used without further purification steps. Yield: 843 mg,4.5 mmol, 98%.
93% With palladium 10% on activated carbon; hydrogen; In ethanol; under 2585.81 Torr; for 22h; A solution of compound 2 (15.0 g, 69.1 mmol) in EtOH (250 mL) was hydrogenation over 10% Pd/C (4.0 g) at 50 psi for 22 h. The catalyst was filtered off through a layer of Celite, and the filtrate was concentrated in vacuo. The crude product was purified by silica gel column chromatography (4:1-3:1 hexanes/EtOAc) to give 3 (12.9 g, 93%) as a pale yellow oil. 1H NMR (DMSO-d6): δ 6.93-6.91 (m, 2H), 5.26 (br s, 2H), 3.87 (s, 3H)
93% With hydrogen;5%-palladium/activated carbon; In methanol; at 25℃; under 2585.81 Torr; for 12h;Inert atmosphere; To a solution of methyl 2,6-difluoro-3-nitrobenzoate (25 g, 1 15 mmol) in MeOH (150 ml_) was added 5% palladium on carbon (2.5 g). The mixture was stirred under H2 atmosphere (50 psi/25 C) for 12 h. The reaction mixture was filtered, and the filtrate was concentrated under the reduced pressure to give the product. 20 g (93 % yield) 1 H NMR (400 MHz, DMSO-c/6) δ ppm 6.95-7.10 (m, 2H), 3.86 (s, 3H)
91% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; Step 4: methyl 3-amino-2,6-difluorobenzoateTo a solution of methyl 2,6-difluoro-3-nitrobenzoate (50 g, 0.23 mol) in MeOH (150 mL) was added Pd/C (10%) and the resulting reaction mixture was stirred at room temperature for overnight under H2 atmosphere. The mixture was filtered. The filtrate was concentratd in vacuo to afford the desired product (38.8 g, 91 >).1H NMR (CDCI3): ? 6.84-6.73 (2H, m), 3.94 (3H, s), 3.69 (2H, br).
91% With palladium on activated charcoal; hydrogen; In methanol; at 20℃; To a solution of 2,6-difluoro-3-nitrobenzoate (50 g, 0.23mo 1) in methanol was added palladium on carbon (10%).The resulting mixture was stirred overnight at room temperature under a hydrogen atmosphere, filtered, and the resulting filtrate was concentrated in vacuo to give the title compound (38.8 g, 91%)
With hydrogen;palladium 10% on activated carbon; In ethanol;Inert atmosphere; Step B: 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. To the flask was added EtOH (350 mL, 0.25 M), and H2 gas was passed through the mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The balloons were recharged with H2 gas and the mixture was stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford crude methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g). The material was taken directly onto the next step.
With hydrogen;palladium 10% on activated carbon; In ethanol; 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25 M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass Dulfonamid filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g). The material was taken directly onto the next step.
With hydrogen;palladium 10% on activated carbon; In ethanol; 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. EtOH (350 mL, 0.25 M) was added, and then H2 was passed through the reaction mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The following day the reaction mixture was re-flushed with fresh H2 balloons and stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g). The material was taken directly onto the next step.
With hydrogen;palladium 10% on activated carbon; In ethanol;Inert atmosphere; Step B: 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. To the flask was added EtOH (350 mL, 0.25 M), and H2 gas was passed through the mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The balloons were recharged with H2 gas and the mixture was stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford crude methyl 3-amino-2,6-difiuorobenzoate as an oil (15.66 g). The material was taken directly onto the next step.
With hydrogen;palladium 10% on activated carbon; In ethanol;Inert atmosphere; 10% (wt.) Pd on activated carbon (4.46 g, 4.19 mmol) was added to a 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) under a nitrogen atmosphere. To the flask was added EtOH (350 mL, 0.25 M), and H2 gas was passed through the mixture for 15 minutes. The reaction mixture was stirred under two H2 balloons overnight. The balloons were recharged with H2 gas and the mixture was stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, N2 gas was flushed through the reaction mixture. The mixture was then filtered through glass microfibre filter ("GF/F") paper twice. The volatiles were removed to afford crude methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g). The material was taken directly onto the next step.
With iron; acetic acid; In methanol; water; at 110℃; Iron powder (15.5g, 4.0 equiv.) was added to 100 mL of water, and 100 mL of acetic acid was added under stirring, followed by 2,6-difluoro-The 3-nitrobenzoic acid methyl ester compound 2309 (15.0 g, 0.069 mol) was dissolved in ethanol (100 mL) and added with a small amount of acetic acid to aid dissolution.The mixture was slowly added to the above mixed solution and heated to 110C. TLC showed that the reaction was complete. The reaction solution was distilled off under reduced pressure and the residue remainedEthyl acetate was added to the solution, which was filtered. The filtrate was washed with saturated sodium bicarbonate, washed with water, saturated brine, and dried over anhydrous sodium sulfate.This was evaporated to dryness to afford compound 2310 (13.2 g, yield: 100%) which was used in the next step without purification
With palladium 10% on activated carbon; hydrogen; In ethanol; Methyl 2,6-difluoro-3-nitrobenzoate (1.13 g, 5.19 mmol) was dissolved in ethanol (17.0 ml.) and palladium on activated charcoal (10% Pd) (0.055g, 0.052 mmol) was added while stirring. The reaction was flushed with hydrogen until complete consumption of the starting material. The suspension was filtrated and the solvent of the filtrate was removed under vacuum. The residue was purified via flash chromatography (silica, gradient: 100% n-hexane -> n- hexane/ethyl acetate 6/4 v/v). The product was obtained as yellow oil. 1H-NMR (200 MHz, DMSO-de) d 7.00 - 6.82 (m, 2H), 5.26 (s, 2H), 3.86 (s, 3H). 13C-NMR (50 MHz, DMSO- d6) d 162.0, 149.8 (dd, J = 240.7, 5.4 Hz), 146.6 (dd, J = 247.6, 6.5 Hz), 133.7 (dd, J = 12.9, (0255) 2.6 Hz), 1 18.2 (dd, J = 8.9, 6.8 Hz), 1 11.6 (dd, J = 22.0, 3.6 Hz), 1 10.1 (dd, J = 20.0, 16.4 Hz), 52.8. TLC-MS (ESI-): Calculated 187.04 for C8H7F2NO2. Measured 185.6 for [M-H] . HPLC: tR = 3.980 min, purity: 97.4% (254.4 nm), 97.6% (230.4 nm).
With palladium 10% on activated carbon; hydrogen; In ethanol; To a 1 L flask charged with methyl 2,6-difluoro-3-nitrobenzoate (18.2 g, 83.8 mmol) was added 10% wt. Pd on activated carbon (4.46 g, 4.19 mmol) under a nitrogen atmosphere. To the flask was added EtOH (350 mL), and hydrogen was passed through the mixture for 15 minutes. The reaction mixture was stirred under two hydrogen balloons overnight. The balloons were recharged with H2 (g) and the mixture was stirred an additional 4 hours. Upon consumption of the starting material and intermediate hydroxylamine as determined by TLC, nitrogen was flushed through the reaction mixture. The mixture was filtered through glass microfibre filter (GF/F) paper twice. The solution was concentrated to afford crude methyl 3-amino-2,6-difluorobenzoate as an oil (15.66 g). The material was used without further purification.

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  • 2
  • [ 13671-00-6 ]
  • [ 84832-01-9 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid; at 20℃; for 2h; Step 3: methyl 2,6-difluoro-3-nitrobenzoateTo a solution of <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (68.8 g, 0.4 mol) in con. H2SO4 (300 mL) was added potassium nitroperoxous acid (48.5 g, 0.48 mol) for three times and the resulting reaction mixture was stirred at room temperature for 2 hrs. The mixture was droped into ice-water (500 mL) and filtered. The solid was washed with water and dried to afford the desired product (89 g, 100%).1H NMR (DMSC i): ? 8.49-8.43 (1H, m), 7.56-7.51 (1H, m), 3.95 (3H, s).
100% With sulfuric acid; potassium nitrate; at 20℃; for 2h; The 2, 6 - difluoro-benzoic acid methyl ester (68.8g, 0.4 muM) dissolved in concentrated sulfuric acid (300 ml) in, addition of potassium nitrate (48.5g, 0 . 48 muM), continuing stirring at room temperature 2 hours. The resulting reaction solution is poured into crushed ice in slow, filtering, the resulting solid with a large number of washing and drying can be obtained as shown in the title compound (89g, 100%)
98% With sulfuric acid; nitric acid; at 0℃; for 1h; To a solution of compound 1 (21.0 g, 122.0 mmol) in concentrated sulfuric acid (50 mL) was added fuming nitric acid (8 mL) dropwise at 0 C. After the reaction mixture was stirred at 0 C for 1 h, it was poured into ice-water. The precipitate was collected by filtration and rinsed with water to give 2 (26.0 g, 98%) as a white solid, mp 58-60 C. 1H NMR (CDCl3): delta 8.25-8.22 (m, 1H), 7.15-7.11 (m, 1H), 4.01 (s, 3H).
80.6% With sulfuric acid; nitric acid; at 0℃; for 0.5h; Fuming nitric acid (1 1 g, 174 mmol) was added to a solution of methyl 2,6- difluorobenzoate (25 g, 145 mmol) in concentrated sulfuric acid (50 ml_) at 0 C, and the reaction was stirred for 30 min at 0C. The reaction mixture was poured over ice-water. The precipitate was filtered to give the title compound 25.1 g (80.6 % yield) 1H NMR (400 MHz, CDCI3) delta ppm 8.13-8.20 (m, 1 H), 7.02-7.10 (m, 1 H), 3.93 (s, 3H).
64% With sulfuric acid; nitric acid; at 20℃; for 1h;Cooling with ice; Sulfuric acid (37 mL) was slowly added to nitric acid (20 mL) under ice-cooling, and added <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (25.7 g,149 mmol), The reaction was gradually warmed to room temperature and stirring was continued for 1 hour. The reaction system was poured into ice-water and filtered to obtain a white solid compound P'(20.7 g, yield 64%).
64% With sulfuric acid; nitric acid; at 20℃; for 1h;Cooling with ice; Sulfuric acid (37 mL) was slowly added to nitric acid (20 mL) under ice-cooling, and <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (25.7 g, 149 mmol) and the reaction was gradually allowed to warm to room temperature. Stirring was continued for 1 hour, The reaction system was poured into ice-water and filtered to give a white solid compound d (20.7g, yield 64%)
With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 0.583333h; To fuming nitric acid (3.87 mL, 86.6 mmol) at O 0C was slowly added concentrated sulfuric acid (7.27 mL, 136.4 mmol). After stirring for 5 min., <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (3.90 mL, 29.0 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 30 min., the reaction mixture was poured into ice- water, and extracted thrice with dichloromethane. The combined organic portions were washed with saturated aqueous sodium bicarbonate, dried over MgSO4, filtered, and concentrated in vacuo to afford a colorless oil. MS(ES+) m/e 218 [M+eta]+. Upon standing, the oil solidified to a white solid, which was dissolved in ethanol (50.0 mL) and treated with ammonium hydroxide (1.0 mL, 29 % aqueous solution) at ambient temperature. After 4 h, additional ammonium hydroxide (0.8 mL, 29 % aqueous solution) was added and the reaction mixture was stirred overnight. The solution was concentrated and the residual solid was washed with isopropanol, filtered, washed with water, and dried in vacuo to afford the title compound (5.69 g, 92%) as a yellow solid. 1H NMR (400 MHz, DMSO-iie) delta ppm 8.33 (dd, J=9.5, 5.7 Hz, 1 H), 8.11 (br. s., 2 H), 6.62 (t, J=9.9 Hz, 1 H), 3.89 (s, 3 H). MS(ES+) m/e 215 [M+H]+.
With sulfuric acid; nitric acid; at 0 - 20℃; 1a) Methyl 2-amino-6-fluoro-3-nitrobenzoate To fuming nitric acid (3.87 mL, 86.6 mmol) at 0 C. was slowly added concentrated sulfuric acid (7.27 mL, 136.4 mmol). After stirring for 5 min., <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (3.90 mL, 29.0 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 30 min, the reaction mixture was poured into ice-water and extracted thrice with dichloromethane. The combined organic portions were washed with saturated aqueous sodium bicarbonate, dried over MgSO4, filtered, and concentrated in vacuo to afford a colorless oil. MS (ES+) m/e 218 [M+H]+. Upon standing, the oil solidified to a white solid, which was dissolved in ethanol (50.0 mL) and treated with ammonium hydroxide (1.0 mL, 29% aqueous solution) at ambient temperature. After 4 h, additional ammonium hydroxide (0.8 mL, 29% aqueous solution) was added and the reaction mixture was stirred overnight. The solution was concentrated and the residual solid was washed with isopropanol, filtered, washed with water, and dried in vacuo to afford the title compound (5.69 g, 92%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.33 (dd, J=9.5, 5.7 Hz, 1H) 8.11 (br. s., 2H) 6.62 (t, J=9.9 Hz, 1H) 3.89 (s, 3H). MS (ES+) m/e 215 [M+H]+.

  • 3
  • [ 84832-01-9 ]
  • [ 1268830-91-6 ]
 

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