3-Nitrobenzaldehyde → 2,6-Dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) ester

HRID 728323Notes

Reaction equation

HRID 728323 reaction equation
[C:1]([O:7][CH2:8][CH2:9][NH:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20].[NH2:30]/[C:31](/[CH3:40])=[CH:32]\[C:33]([O:35]CCC#N)=[O:34]>C(O)(C)C.C([O-])(=O)C.[NH2+]1CCCCC1>[C:11]([NH:10][CH2:9][CH2:8][O:7][C:1]([C:2]1[CH:25]([C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:32]([C:33]([OH:35])=[O:34])=[C:31]([CH3:40])[NH:30][C:3]=1[CH3:5])=[O:6])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1

Participants

6

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 104447842-Nicotinoylaminoethyl acetoacetateHCID 136714102-Cyanoethyl 3-aminocrotonate

Product 1

HCID 100960672,6-Dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) esterYield 97.1%

Reagents, catalysts & solvents 2

HCID 3014295Piperidinium acetateCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 25.03 g (100 mole) of 2-nicotinoylaminoethyl acetoacetate, 15.11 g (100 mmole) of m-nitrobenzaldehyde and 15.42 g (100 mmole) of 2-cyanoethyl 3-aminocrotonate in 150 ml of isopropyl alcohol was added 0.73 g (5 mmole) of piperidinium acetate, and the mixture was refluxed for 5 hours. After evaporation of the solvent, the residue was dissolved in 200 ml of acetone. To the solution was added 200 ml of 0.75 N aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for an hour. 1N hydrochloric acid was added, and the solution was concentrated and extracted with chloroform Evaporation of the solvent gave 45.27 g of 2,6-dimethyl4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nicotinoylaminoethyl) ester.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in 200 ml of acetone
  4. additionTo the solution was added 200 ml of 0.75 N aqueous sodium hydroxide solution
  5. addition1N hydrochloric acid was added
  6. concentrationthe solution was concentrated
  7. extractionextracted with chloroform Evaporation of the solvent

Sources & evidence

ORD record
ord-526c5c6affdf45878ead785ba8efd3b8
Source dataset
uspto-grants-1991_09
Patent number
US05047543

Reaction notes

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