Ethanol → 2-Pyrrolidino-4,6-dimethyl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1077034Notes

Reaction equation

HRID 1077034 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([CH:8]=CC)=O)[CH3:2].[CH2:12]([O:14][C:15](=[O:24])[CH:16]=[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[NH2:18])[CH3:13].[CH2:25](O)[CH3:26]>>[CH2:12]([O:14][C:15]([C:16]1[CH:6]([CH3:8])[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:11])[C:25]([CH3:26])=[N:18][C:17]=1[N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:24])[CH3:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 53428592Ethylideneacetoacetic acid ethyl esterHCID 706080083-Pyrrolidino-3-aminoacrylic acid ethyl ester

Product 1

HCID 706082732-Pyrrolidino-4,6-dimethyl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 42%

Procedure

Boiling a solution of 7.8 g of ethylideneacetoacetic acid ethyl ester and 9.2 g of 3-pyrrolidino-3-aminoacrylic acid ethyl ester in 100 ml of ethanol for 2 hours and distilling the residue yields 2-pyrrolidino-4,6-dimethyl-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester of boiling point (1.5 mm. Hg : 199° - 204°C). Yield: 42% of theory.

Workup

  1. customfor 2 hours
  2. distillationdistilling the residue

Sources & evidence

ORD record
ord-62f2a39d365f42a9b25b3b5eeb63be01
Source dataset
uspto-grants-1976_05
Patent number
US03959292

Reaction notes

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