3-Nitrobenzaldehyde → 2-Pyrrolidino-6-methyl-4-(3-nitrophenyl)-5-acetyl-4,5-dihydropyridine-3-carboxylic acid ethyl ester

HRID 2163725Notes

Reaction equation

HRID 2163725 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([CH2:15][C:16](=[O:18])[CH3:17])(=O)[CH3:13].[CH2:19]([O:21][C:22](=[O:31])[CH:23]=[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[NH2:25])[CH3:20].C(O)(C)C.CCOCC>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:15]([C:16](=[O:18])[CH3:17])[C:12]([CH3:13])=[N:25][C:24]=1[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:31])[CH3:20]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 31261AcetylacetoneHCID 22147583Diethyl ether 2-propanolHCID 706080083-Pyrrolidino-3-aminoacrylic acid ethyl ester

Product 1

HCID 706080942-Pyrrolidino-6-methyl-4-(3-nitrophenyl)-5-acetyl-4,5-dihydropyridine-3-carboxylic acid ethyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heating a solution of 7.6 g of 3-nitrobenzaldehyde, 5.0 g of acetylacetone and 9.2 g of 3-pyrrolidino-3-aminoacrylic acid ethyl ester in 50 ml of ethanol for 2 hours yields 2-pyrrolidino-6-methyl-4-(3-nitrophenyl)-5-acetyl-4,5-dihydropyridine-3-carboxylic acid ethyl ester of melting point 130° C. (isopropanol/ether).

Sources & evidence

ORD record
ord-136963fea5da45fe91f56905d5b9a640
Source dataset
uspto-grants-1979_01
Patent number
US04136187

Reaction notes

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