Ethanol → 2-Phthalimidomethyl-6-methyl-4-(-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1449016Notes

Reaction equation

HRID 1449016 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](C=O)=[CH:3][CH:2]=1.[CH2:9]([O:11][C:12](=[O:28])[CH2:13][C:14]([CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])=O)[CH3:10].[CH2:29]([O:31][C:32](=[O:37])/[CH:33]=[C:34](\[NH2:36])/[CH3:35])[CH3:30].[CH2:38](O)C>>[CH2:9]([O:11][C:12]([C:13]1[CH:38]([C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][N:1]=2)[C:33]([C:32]([O:31][CH2:29][CH3:30])=[O:37])=[C:34]([CH3:35])[NH:36][C:14]=1[CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])=[O:28])[CH3:10]

Participants

5

Reactant 4

HCID 702EthanolHCID 133894-PyridinecarboxaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 701239Ethyl 4-(1,3-dioxoisoindolin-2-YL)-3-oxobutanoate

Product 1

HCID 705901212-Phthalimidomethyl-6-methyl-4-(-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 65%

Procedure

A solution of 5.2 ccs of pyridine-4-aldehyde, 14.0 g of phthalimidoacetoacetic acid ethyl ester and 6.5 g of β-aminocrotonic acid ethyl ester in 80 ccs of ethanol is heated under reflux for 24 hours and, after cooling and filtering, white crystals of melting point 205°-207° C. (ethanol) are obtained, yield: 65%.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureafter cooling
  3. filtrationfiltering
  4. customwhite crystals of melting point 205°-207° C. (ethanol) are obtained

Sources & evidence

ORD record
ord-170bfcbb28e34d00a67af31d6ea106fa
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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