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Quality Control of [ 4803-74-1 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 4803-74-1 ]

CAS No. :	4803-74-1
Formula :	C₁₇H₁₅NO₃
M.W :	281.31
SMILES Code :	O=C1/C(CC2=C1C=C(OC)C(OC)=C2)=C/C3=CC=NC=C3
MDL No. :	MFCD08458868
InChI Key :	SUVQWDLUAIFZKM-NTUHNPAUSA-N
Pubchem ID :	11572727

Safety of [ 4803-74-1 ]

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

Calculated chemistry of [ 4803-74-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	21
Num. arom. heavy atoms	12
Fraction Csp3	0.18
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	79.88
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.42 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.56
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.81
Log P_o/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.	1.42
Log P_o/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	3.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.48
Solubility	0.0921 mg/ml ; 0.000328 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.	-3.33
Solubility	0.132 mg/ml ; 0.00047 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	-5.54
Solubility	0.000806 mg/ml ; 0.00000286 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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	Yes
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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.13 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	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<0.0
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)	2.7

Application In Synthesis [ 4803-74-1 ]

* 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 [ 4803-74-1 ]

[ 4803-74-1 ] Synthesis Path-Downstream 1~26

2
[ 872-85-5 ]
[ 2107-69-9 ]
[ 4803-74-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium hydroxide; In water; at 25 - 30℃; for 3h;Product distribution / selectivity;	Example 1: Process for preparation of 5,6-dimethoxy-2-(4-pyridylmethylene)-l- indanone of formula IVTo a 1 liter round bottom flask equipped with a mechanical stirrer, thermometer pocket, addition funnel and a condenser, charged demineralized water (250ml), 5,6- dimethoxy-l-indanone (25g) and pyridine-4-carboxaldehyde (19.5g). The reaction mixture was stirred for 5 minutes at a temperature of 25C to 30C. To the reaction mixture then charged a solution of potassium hydroxide (5.2g) dissolved in demineralized water (125ml) slowly over period of 2 hours at a temperature of 25 C to 30C. The reaction mixture was further maintained at a temperature of 25C to 30C for 1 hour to obtain the product, 5,6-dimethoxy-2-(4-pyridylmethylene)-l- indanone. The product obtained was then filtered and washed with demineralized water. Dry the product under vacuum at a temperature of 50C to 55C for 10 hours. Yield: 98%Purity: 99.71%
95.8%		5, 6 Dimethoxy indanone (100 grams), Pyridine-4-carboxaldehyde (78.0 grams) and p-toluene sulfonic acid (138.4 grams) were suspended in toluene (1250 ml) and heated to reflux using water separator for 6 hours. The resulting mass was cooled to 25-40 C. and the solid was filtered off under suction. Further the wet solid was suspended in aqueous 10% sodium carbonate solution (1200 ml) and stirred for 30-60 minutes. The resulting pale yellow precipitate solid was filtered off under suction, washed with water (1000 ml) and dried at a temperature of 80 C. to afford 5,6 Dimethoxy-2-(pyridin-4yl)-methylene-indan-lone (Weight: 140 grams, 95.8%).
92.2%	With potassium iodide; calcium chloride; In acetone; at 40 - 50℃; for 4h;	In a three-necked flask equipped with a condenser and a stirrer, acetone 60 mL, 5,6-dimethoxy-1-indanone was sequentially added.9.6g, anhydrous calcium chloride 5.55g (0.05mol), 4-pyridine formaldehyde 5.89g, potassium iodide 0.96g, stirred at 40 ~ 50 CAfter mixing for 4 h, the basic reaction was completely monitored by HPLC, cooled to room temperature, filtered, and the filtrate was concentrated.Filtration and drying under vacuum gave Compound III 12.96 g, yield 92.2%, HPLC, purity 99.7%.

67%	With sodium hydroxide; In ethanol; water; at 20℃;Inert atmosphere;	To a solution of 1 mmol of 4-pyridinecarboxaldehyde and 1 mmol of 5,6-dimethoxy-1-indanone in 10 ml EtOH, aqueous solution of NaOH (10%) was added dropwise. The reaction mixture was stirred overnight at room temperature. The obtained solid was fltered and recrystallized from EtOH to give 3 as an of-white solid [22]; yield 67%; mp: 118-120 C; FTIR (KBr) nu3008, 2937, 1691, 1600, 1465, 1315, 1268, 1029 cm-1; 1H NMR (400 MHz, CDCl3): 3.82 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.03 (2H, s, CH2), 7.17 (1H, s, Ar), 7.22 (1H, s, Ar), 7.42 (1H, s, =CH), 7.67 (2H, d, 3JH-H = 5.36, pyridine-H), 8.64 (2H, d, 3JH-H = 5.46, pyridine-H).
	With toluene-4-sulfonic acid; In toluene; for 6h;Heating / reflux;	Preparation 1 Preparation of 5, 6-dimethoxy-2- (pyridine-4-yl) methylene-indan-1-one A mixture OF 5, 6-DIMETHOXY-INDAN-1-ONE (100G), pyridine-4-carboxaldehyde (67g), p- toluene sulfonic acid (118G) in toluene (1200ML) was refluxed azeotropically for 6 hours. The reaction mixture was cooled to room temperature and filtered. The wet solid so obtained was stirred with 10% aqueous sodium carbonate solution. The solid was filtered, washed with acetone and then dried to get the title compound (130G). HPLC Purity: 99.5%
	With sodium hydroxide; In methanol; at 20℃; for 4h;	General procedure: 5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (0.001 mol) with appropriate aldehyde (0.001 mol) in diluted methanolic sodium hydroxide solution was stirred under room temperature for 4 h. The resulting solution was allowed to stand overnight and then the reaction mixture was poured into cold water and neutralized with dilute HCl. The solid was filtered, dried and recrystallized with ethanol furnished the 2-substituted-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one.

References: [1]Patent: WO2012/131540,2012,A1 .Location in patent: Page/Page column 16.
[2]Patent: US2004/143121,2004,A1 .Location in patent: Page 3.
[3]Patent: CN109651234,2019,A .Location in patent: Paragraph 0037-0042; 0055-0062.
[4]Journal of the Iranian Chemical Society,2020,vol. 17,p. 593 - 600.
[5]Patent: WO2004/82685,2004,A1 .Location in patent: Page/Page column 9.
[6]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5694 - 5697.
[7]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.
[8]Journal of Enzyme Inhibition and Medicinal Chemistry,2013,vol. 28,p. 644 - 650.

3
[ 4803-74-1 ]
[ 861675-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; acetic acid;5%-palladium/activated carbon; In methanol; at 60 - 65℃; under 2280.15 - 3040.2 Torr; for 8h;	5,6-Dimethoxy-2-(pyridin-4-yl) methylene indan-1-one (IV, 50.0 grams), 5% palladium on activated carbon (12.5 grams), acetic acid (12.8 grams) and Methanol (875 ml) were taken in 2.0 liter hydrogenation flask and applied hydrogen gas in inert atmosphere. The hydrogenation was carried out at hydrogen pressure of 3-4 atmospheres at 60-65 C. for 8 hours. Then the flask was cooled to room temperature and the catalyst was filtered off. The solvent was distilled off from the filtrate and resulting residue was dissolved in water (1000 ml). The aqueous solution thus obtained was washed with Dichloromethane. Further, the pH of the aqueous layer was adjusted to 13.0 and extracted the compound into Dichloromethane. The combined dichloromethane layer was dried over sodium sulfate and concentrated under vacuum to get the residue. Thus resulted residue was triturated petroleum ether to afford 5,6 Dimethoxy-2-piperidinyl-4-yl methyl-indan-lone (Weight: 49 grams, 95.3%).

References: [1]Patent: US2004/143121,2004,A1 .Location in patent: Page 3.

4
[ 4803-74-1 ]
[ 4803-57-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	With hydrogen;platinum(IV) oxide; In acetic acid; at 80℃; under 760.051 Torr; for 6h;	Example 5 2,3-dihydro-5,6-dimethoxy-2-((pyridin-4-yl)methyl)inden-1-one 1.80 g of <strong>[4803-74-1]2,3-dihydro-5,6-dimethoxy-2-((pyridin-4-yl)methylene)inden-1-one</strong> and 40 milligrams of PtO2 were added to 15 mL glacial acetic acid. The reaction mixture was stirred at 80 C., with H2 being supplied at 1 atmosphere for 6 hours. Solids were filtered off. The filtrate was concentrated. 30 mL of Na2CO3 aqueous solution were added thereto. The resulted mixture was extracted with of chloroform (5*20 mL). The extracts were combined, washed with brine, and dried over anhydrous MgSO4. The drying agent was then filtered off. Solvent was removed in vacuo to give crude product. Purification of crude product by silica gel column chromatography (CHCl3/CH3OH 95/5) afforded 0.63 g of white crystalline compound. The yield was 35%. 1H NMR (CDCl3): 8.53(brs, 2H), 7.15-7.25 (m, 3H), 6.82(s, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 3.35 (dd, 1H, J=4.4, 14.0 Hz), 3.12(dd, 1H, J=7.6, 16.8 Hz), 2.95-3.05 (m, 1H), 2.65-2.75 (m, 2H).
	With hydrogen;5%-palladium/activated carbon; In methanol; dichloromethane; under 1500.15 Torr; for 3h;	The mixture of 5, 6-DIMETHOXY-2- (4-PYRIDYL) METHYLENE-1-INDANONE (34 gm), methanol (325 ML), METHYLENEDICHLORIDE (200 ml) and 5% palladium- charcoal (2 gm) is taken in a hydrogenation flask and subjected to hydrogenation under a hydrogen pressure of 2 bars for 3 hours. The catalyst is removed by filtration and the solvents are evaporated completely under vacuum to obtain a residue. Ethyl acetate (150 ml) is added to the residue and stirred for 20 minutes at 25C to 30C. The contents are then cooled to 0C, stirred for 30 minutes and filtered to give 34 gm of 5, 6-DIMETHOXY-2- (4-PYRIDYL) METHYL-1- indanone.
	With hydrogen;palladium 10% on activated carbon; In methanol; dichloromethane; under 760.051 Torr; for 5h;	Example 1 Preparation of 5, 6-dimethoxy-2- (4-pyridyl) methyl-indan-1-one. 5, 6-DIMETHOXY-2- (PYRIDINE-4-YL) METHYLENE-INDAN-1-ONE (100G, from preparation 1) was hydrogenated using 10% Palladium/carbon (LOG, 50% moisture) in a mixture of methanol (1500ML) and methylene chloride (1000ML) at atomospheric pressure. The hydrogen gas was bubbled into the reaction mixture for about 5 hours. The reaction mixture was filtered and the filtrate was concentrated to get the title compound (92 g). HPLC Purity: 99.8%.

References: [1]Patent: US2007/72905,2007,A1 .Location in patent: Page/Page column 5.
[2]Patent: WO2005/3092,2005,A1 .Location in patent: Page 10-11.
[3]Patent: WO2004/82685,2004,A1 .Location in patent: Page/Page column 9.

5
[ 4803-74-1 ]
[ 1034439-43-4 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3588 - 3598.

6
[ 872-85-5 ]
[ 2747-08-2 ]
[ 4803-74-1 ]
5,6-dimethoxy-3-(pyridine-4-yl)spiro[indene-2,2'-oxiran]-1(3H)-one [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 1157 - 1160.

7
[ 872-85-5 ]
[ 2747-08-2 ]
[ 4803-74-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,2010,vol. 58,p. 1157 - 1160.

8
[ 4803-74-1 ]
[ 17433-93-1 ]
[ 1346911-31-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid; for 12h;Reflux;	General procedure: To a 2-substituted-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one (3a-g) (0.01 mol) and substituted phenyl semicarbazide (0.01 mol) in 20 ml glacial acetic acid was refluxed for 12 h. The excess of solvent was removed under reduced pressure and then the reaction mixture was poured into the crushed ice. The solid mass was filtered dried and recrystallized with ethanol furnished the 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5694 - 5697.

9
[ 4803-74-1 ]
[ 69194-89-4 ]
[ 1346911-17-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With acetic acid; for 12h;Reflux;	General procedure: To a 2-substituted-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one (3a-g) (0.01 mol) and substituted phenyl semicarbazide (0.01 mol) in 20 ml glacial acetic acid was refluxed for 12 h. The excess of solvent was removed under reduced pressure and then the reaction mixture was poured into the crushed ice. The solid mass was filtered dried and recrystallized with ethanol furnished the 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5694 - 5697.
[2]Journal of Enzyme Inhibition and Medicinal Chemistry,2013,vol. 28,p. 644 - 650.
[3]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

10
[ 4803-74-1 ]
[ 4426-72-6 ]
[ 1346911-48-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With acetic acid; for 12h;Reflux;	General procedure: To a 2-substituted-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one (3a-g) (0.01 mol) and substituted phenyl semicarbazide (0.01 mol) in 20 ml glacial acetic acid was refluxed for 12 h. The excess of solvent was removed under reduced pressure and then the reaction mixture was poured into the crushed ice. The solid mass was filtered dried and recrystallized with ethanol furnished the 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5694 - 5697.
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

11
[ 4803-74-1 ]
[ 100-39-0 ]
[ 178551-26-3 ]

Yield	Reaction Conditions	Operation in experiment
	In butanone; at 115 - 117℃; for 3h;Reflux;Product distribution / selectivity;	Example 4: l-benzyl-4-[(5,6-dimethoxy-l-indanone-2-yl)methylene]pyridinium bromide of formula VTo a round bottom flask equipped with mechanical stirrer, thermometer pocket, addition funnel and condenser, charged methyl isobutyl ketone (1200ml) and 5,6- dimethoxy-2-(4-pyridylmethylene)-l -indanone (lOOg). The reaction mixture was then refluxed at a temperature of 115C to 117C. To the refluxing reaction mixture then added benzyl bromide (75.5g) dropwise over a period of 30 minutes. The reaction mixture stirred further for 2.5 hours. Cooled the reaction mixture at a temperature of 25C to 28C to obtain the product, l-benzyl-4-[(5,6-dimethoxy-l-indanone-2- yl)methylene]pyridinium bromide. Filter the product obtained and washed with methyl isobutyl ketone. Dry the product under vacuum at a temperature of 50C to 55C for 1-2 hours.Yield: 98.76% Purity: 97.5%

References: [1]Patent: WO2012/131540,2012,A1 .Location in patent: Page/Page column 17-18.

12
[ 4803-74-1 ]
[ 153885-60-0 ]
[ 1321920-29-9 ]

References: [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2013,vol. 28,p. 644 - 650.
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

13
[ 4803-74-1 ]
[ 2646-26-6 ]
[ 1321920-36-8 ]

References: [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

14
[ 4803-74-1 ]
[ 1094769-79-5 ]
[ 1321920-42-6 ]

References: [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2013,vol. 28,p. 644 - 650.
[2]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

15
[ 4803-74-1 ]
N-(2,4-dimethylphenyl)semicarbazide [ No CAS ]
[ 1333385-51-5 ]

References: [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

16
[ 4803-74-1 ]
[ 79-19-6 ]
[ 1333385-63-9 ]

References: [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 7029 - 7035,7.

17
[ 4803-74-1 ]
5,6-dimethoxy-2-[(4-piperidinyl)methyl]-2,3-dihydro-1-indenone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.1%		60 mL of absolute ethanol was added to a 500 mL three-necked flask, 11.24 g of compound III was added, and ammonium formate 20.16 g was added.(0.32 mol), 10.2 g of 10% palladium on carbon, and the reaction was stirred at a temperature of 40-50 C. After 1.5 h, the reaction was completely detected by HPLC, and Pd/C was filtered off.The filtrate was concentrated, 80 mL of dichloromethane was added, and concentrated hydrochloric acid was added thereto under stirring to adjust the pH to 4.5, crystallized for 2 h, filtered, and dried in vacuo.Compound IV 11.71 g, yield 90.1%, purity by HPLC was 99.5%.

References: [1]Patent: CN109651234,2019,A .Location in patent: Paragraph 0043-0048; 0063-0066.

18
[ 4803-74-1 ]
[ 64-19-7 ]
C₁₇H₁₇NO₃*C₂H₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.8%	With 5%-palladium/activated carbon; hydrogen; In methanol; at 55 - 60℃; under 6000.6 - 7500.75 Torr;Large scale;	(1) Reaction process:300 kg of 4-[(5,6-dimethoxy-1-indolone)-2-methylene]-methylpyridine was dissolved in 1800 kg of methanol, and 120 kg of acetic acid mixture was added thereto, and 7.5 kg of 5% palladium carbon was added. , vacuuming, replacing three times with nitrogen, hydrogenating to 0.8-1.0 MPa, heating to 55-60 C, until the raw material reaction is complete;(2) Post-processing:The reaction solution was filtered, and the filtrate was concentrated to dryness under reduced pressure. 1500 kg of ethyl acetate was added while hot, and the mixture was cooled to 0-10 C, stirred and crystallized, filtered, and dried.4-[(5,6-Dimethoxy-1-indolone)-2-methylene]piperidine acetate 312.3 kg, the yield was 83.8%, and the liquid phase purity was 99.90%.

References: [1]Patent: CN110183375,2019,A .Location in patent: Paragraph 0019; 0020; 0021.

19
[ 4803-74-1 ]
[ 823-78-9 ]
1-(3-bromobenzyl)-4-[(5,6-dimethoxy-1-indanone-2-ylidene)methyl]pyridinium bromide [ No CAS ]