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Chemical Structure| 6311-37-1 Chemical Structure| 6311-37-1

Structure of 4-Amino-3-bromobenzoic acid
CAS No.: 6311-37-1

Chemical Structure| 6311-37-1

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Product Details of [ 6311-37-1 ]

CAS No. :6311-37-1
Formula : C7H6BrNO2
M.W : 216.03
SMILES Code : O=C(O)C1=CC=C(N)C(Br)=C1
MDL No. :MFCD03407439
InChI Key :BFIVZIVVJNFTIQ-UHFFFAOYSA-N
Pubchem ID :238935

Safety of [ 6311-37-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 6311-37-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 45.51
TPSA ?

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

63.32 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.23
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

1.5
Log Po/w (WLOGP)?

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

1.74
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.

0.64
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

1.18
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.26

Water Solubility

Log S (ESOL):?

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

-2.46
Solubility 0.746 mg/ml ; 0.00345 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.

-2.44
Solubility 0.789 mg/ml ; 0.00365 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

-2.27
Solubility 1.16 mg/ml ; 0.00536 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.

-6.55 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.

0.56

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

1.0 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)

 1.26

Application In Synthesis of [ 6311-37-1 ]

* 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 [ 6311-37-1 ]

[ 6311-37-1 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 6311-37-1 ]
  • 4-amino-3-mercapto-benzoic acid-(2-diethylamino-ethyl ester) [ No CAS ]
  • 2
  • [ 74103-28-9 ]
  • [ 6311-37-1 ]
  • 3
  • [ 150-13-0 ]
  • [ 6311-37-1 ]
YieldReaction ConditionsOperation in experiment
70% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18h; 4-Amino-benzoic acid (100 mmol) was dissolved in DMF (50 mL) and iV-bromosuccinimide(100 mmol) was added. Stirred at ambient temperature for 18h, the reaction mixture was then poured into water (100 mL). The product was removed by filtration, washed with water and dried in vacuo to give 4-amino-3-bromo-benzoic acid.Yield: 70%IH NMR (D6-DMSO): 6.10 (s, 2H); 6.78 (d, IH); 7.63 (dd, IH); 7.89 (d, IH); 12.39 (br s,IH).
65 - 70% With N-Bromosuccinimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 18h; 4-Amino-benzoic acid (100 mmol) was dissolved in DMF (50 mL) and N-bromo- succinimide (100 mmol) was added. Stirred at ambient temperature for 18h, the reaction mixture was then poured into water (100 mL). The product was removed by filtration, washed with water and dried in vacuo. Yield: 70% 1H NMR (D6-DMSO) : 6.10 (s, 2H); 6.78 (d, 1H); 7.63 (dd, 1H); 7.89 (d, 1H) ; 12.39 (br s, 1H).4-Amino-benzoic acid (100 mmol) was dissolved in DMF (100 mL) and N-bromo succinimide (100 mmol) was added portion wise. The orange reaction mixture was stirred over night at ambient temperature, then poured into water. The product was collected by filtration and re-crystallized from MeOH. Yield: 65% 1H NMR (D6-DMSO) : 6.09 (s, 2H); 6.81 (d, 1H); 7.13 (dd, 1H); 7.89 (d, 1H) ; 12.37 (br, 1H).
61% With hydrogen bromide; 2-methylpyridinium nitrate; at 90℃; for 12h;Green chemistry; General procedure: To a round bottom flask was added 5 mmol of acetophenone, 0.5 mmol of 2-methylpyridine nitrate and 5.5 mmol of 40 wt% HBr, 60 C under the open flask stir reaction 6h, The yield of alpha-bromoacetophenone was 95% The product was isolated by silica gel column chromatography (ethyl acetate / boiling point 60-90 C petroleum ether) at 200-300 mesh, The isolated yield was 88%.
  • 4
  • [ 6311-37-1 ]
  • [ 107-07-3 ]
  • 4-amino-3-bromo-benzoic acid-(2-chloro-ethyl ester) [ No CAS ]
  • 5
  • [ 6311-37-1 ]
  • (2R,4S)-2-Amino-4-fluoro-pentanedioic acid diisopropyl ester; hydrochloride [ No CAS ]
  • [ 194809-38-6 ]
  • 6
  • [ 10035-10-6 ]
  • [ 7722-84-1 ]
  • [ 150-13-0 ]
  • [ 6311-37-1 ]
  • [ 4123-72-2 ]
  • 9
  • [ 6311-37-1 ]
  • 3-(6-iodo-quinolin-8-yl)-phenylamine [ No CAS ]
  • 10
  • [ 6311-37-1 ]
  • 8-(3-iodo-phenyl)-quinolin-6-ylamine [ No CAS ]
  • 11
  • [ 6311-37-1 ]
  • 8-(3-nitro-phenyl)-quinolin-6-ylamine [ No CAS ]
  • 12
  • [ 6311-37-1 ]
  • 6-iodo-8-(3-nitro-phenyl)-quinoline [ No CAS ]
  • 13
  • [ 6311-37-1 ]
  • 6-azido-8-(3-iodo-phenyl)-quinoline [ No CAS ]
  • 14
  • [ 6311-37-1 ]
  • 8-(3-azido-phenyl)-6-iodo-quinoline [ No CAS ]
  • 15
  • [ 6311-37-1 ]
  • 8-(3-iodo-phenyl)-6-isocyanato-quinoline [ No CAS ]
  • 16
  • [ 6311-37-1 ]
  • 6-isocyanato-8-(3-nitro-phenyl)-quinoline [ No CAS ]
  • 17
  • [ 6311-37-1 ]
  • 8-(3-amino-phenyl)-quinoline-6-carboxylic acid [ No CAS ]
  • 18
  • [ 6311-37-1 ]
  • [ 309250-39-3 ]
  • 19
  • [ 6311-37-1 ]
  • [ 309250-42-8 ]
  • 20
  • [ 6311-37-1 ]
  • (2S,4R)-2-{3-Bromo-4-[(2,4-diamino-pteridin-6-ylmethyl)-amino]-benzoylamino}-4-fluoro-pentanedioic acid [ No CAS ]
  • 21
  • [ 6311-37-1 ]
  • [ 194809-40-0 ]
  • 22
  • [ 6311-37-1 ]
  • 4-amino-3-bromo-benzoic acid-(2-diethylamino-ethyl ester) [ No CAS ]
  • 23
  • [ 6311-37-1 ]
  • [ 98-80-6 ]
  • [ 849208-76-0 ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In diethylene glycol dimethyl ether; water; for 18h;Heating / reflux; 4-Amino-3-bromo-benzoic acid (65 mmol), phenyl boronic acid (70 mmol), Pd (PPh3) 2Cl2 (3.2 mmol) and IZ2COs (140 mmol) was combined in a flask and refluxed in a mixture of ethylene glycol dimethyl ether (75 mL) and water (75 mL) under an argon atmosphere for 18h. The organic solvent was removed in vacuo and pH was adjusted to 4. The crude product was removed by filtration, re-dissolved in ethyl acetate, and passed through a silica plug to remove any Pd-residues. The filtrate was evaporated to dryness and re-crystallized from ethyl acetate/heptane to give off-white crystals. Yield: 47% NMR (D6-DMSO) : 5.56 (s, 2H); 6.78 (d, 1H); 7.30-7. 75 (8H); 12.09 (br, 1H).
  • 24
  • [ 96-50-4 ]
  • [ 6311-37-1 ]
  • [ 851202-79-4 ]
YieldReaction ConditionsOperation in experiment
33% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane; at 60℃; 4-Amino-3-bromo-benzoic acid (18.5 mmol) was dissolved in DMF (10 mL) and 1,2-dichloroethane (80 mL). DIPEA (18.5 mmol), 1- (3-dimethylaminopropyl)- 3-ethyl-carbodiimide hydrochloride (18.5 mmol), 1-hydroxybenzotriazole (18.5 mmol) and 2-aminothiazole (18. 5 mmol) was added and the reaction mixture was stirred at 60 C over night. The volume was reduced in vacuo, and water (60 mL) was added. The mixture was extracted with ethyl acetate, the organic phase was washed with NH4C1 (aq. , sat. ), dried over MgS04, filtered and evaporated. The crude product was purified by flash chromatography on silica using gradient elution (heptane/ethyl acetate). Yield: 33% (23% overall) 1H NMR (D6-DMSO) : 6.14 (s, 2H); 6.82 (d, 1H); 7.21 (d, 1H); 7.51 (d, 1H); 7.86 (dd, 1H); 8.22 (d, 1H); 12.24 (br s, 1H).
33% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 60℃; 4-Amino-3-bromo-benzoic acid (18.5 mmol) was dissolved in DMF (10 mL) and1,2-dichloroethane (80 mL). DIPEA (18.5 mmol), l-(3-dimethylaminopropyl)-3-ethyl- carbodiimide hydrochloride (18.5 mmol), 1-hydroxybenzotriazole (18.5 mmol) and 2- EPO <DP n="39"/>aminothiazole (18.5 mmol) was added and the reaction mixture was stirred at 60 C over night. The volume was reduced in vacuo, and water (60 mL) was added. The mixture was extracted with ethyl acetate, the organic phase was washed with NH4Cl (aq., sat.), dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica using gradient elution (heptane/ethyl acetate). Yield: 33% (23% overall)IH NMR (D6-DMSO): 6.14 (s, 2H); 6.82 (d, IH); 7.21 (d, IH); 7.51 (d, IH); 7.86 (dd, IH); 8.22 (d, IH); 12.24 (br s, IH).
  • 25
  • [ 106896-49-5 ]
  • [ 6311-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With lithium hydroxide; water; In tetrahydrofuran; SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a <n="13"/>benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,
  • 26
  • [ 6311-37-1 ]
  • [ 128828-52-4 ]
  • [ 1032373-87-7 ]
YieldReaction ConditionsOperation in experiment
With dacarbazine;dmap; In dichloromethane; SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 ,8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI2(dppf) as a catalyst, created compounds 51a followed by reductive amination utilizing N-Boc- aminoacetaldehyde produced compounds 52a-c. A series of deprotections followed by guanidinylation of the resulting amine afforded the N-terminal portions of the inhibitor 53a-c. The C-terminal hydrophobic portion of the molecule was synthesized via alkylation of A- nitroaniline with the corresponding bromide and subsequent reduction of the nitro group utilizing tin (II) chloride, producing compounds 55a-i. Coupling of compounds 53a-c and 55a- i followed by Boc deprotection under acidic conditions produced inhibitors 56aa-ci. Inhibitors64a-b were derived from a similar synthesis, but in place of the reductive amination step, 48c was reacted with Boc-Gly-OH to provide the amide intermediate compound 62 which was manipulated in a similar manner to provide inhibitors 64a-b, seen in Figure 16.The synthesis of inhibitors 57aa-fa was designed to employ a late stage Suzuki coupling to provide faster access to a number of derivatives at the R1 position, while keeping R2 as a <n="13"/>benzyl substituent, see Figure 15. Commercially available methyl-4-amino-3-bromobenzoate was saponified under basic conditions followed by amide bond formation with compound 55a to provide compound 59a. This intermediate was then reacted with different boronic acid derivatives PdCI2(dppf) as a catalyst to provide 60aa-fa. A series of functional group transformations provided inhibitors 57aa-fa. The indole scaffold was readily derived from commercially available 4-iodoaniline and Boc- GIy-OH, which were reacted to form iodo-amide compound 65, seen in Figure 17. Sonagashira cross-coupling of compound 65 and ethynyl-trimethyl-silane (TMS-acetylene) followed by removal of the silyl protecting group afforded terminal alkyne compound 66. A consecutive Sonagashira cross-coupling with 2-iodo-4-nitroaniline followed by cycloisomerization employing catalytic copper (II) acetate41 afforded indole scaffold compound 68. Reduction of the nitro to the amine followed by alkylation with the cooresponding bromide provided compound 70a-b. A series of functional group transformations, similar to the reactions depicted in Figures 10 and 13, provided inhibitors 71a-b. It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween. Now that the invention has been described,
  • 27
  • [ 150-13-0 ]
  • [ 6311-37-1 ]
  • [ 4123-72-2 ]
  • 28
  • [ 6311-37-1 ]
  • 2-bromo-4-carboxyphenyldiazonium tetrafluoroborate [ No CAS ]
  • 29
  • [ 6311-37-1 ]
  • (4-amino-3-bromo-phenyl)-methanol [ No CAS ]
  • 30
  • [ 6311-37-1 ]
  • [ 4123-72-2 ]
  • 31
  • [ 124-13-0 ]
  • [ 6311-37-1 ]
  • [ 1344028-85-8 ]
YieldReaction ConditionsOperation in experiment
93% With alpha-picoline-borane; In methanol; at 20℃; General procedure: 4-amino-3-methoxybenzoic acid (4b) (~3 mmol) was dissolved in 15 mL methanol with alpha-picoline-borane (1.1 mol eq) and butanal (1.1 mol eq). The reaction was stoppered with a vent needle and stirred overnight at room temperature. After 16-24 h, solvent was removed in vacuo, 10 mL 1 M HCl was added to the flask, and stirred at room temperature for an additional 30 min. The pH was adjusted to neutral using NaHCO3 and the intermediate product was extracted with ethyl acetate (2 60 mL). The organic layer was washed with brine (1x 45 mL), dried with magnesium sulfate, filtered, removed in vacuo, and subsequently purified via column chromatography with 30% ethyl acetate in hexane to yield 3 (84%).
  • 32
  • [ 6311-37-1 ]
  • [ 1344029-03-3 ]
  • 33
  • [ 6311-37-1 ]
  • C18H24BrN3O [ No CAS ]
 

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A300530 [4123-72-2]

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A641970 [42237-85-4]

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5-Amino-2-bromobenzoic acid

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Carboxylic Acids

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