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

HRID 1449009

Reaction equation

HRID 1449009 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.C(OC(=O)CC([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)C.[CH2:29]([O:31][C:32](=[O:37])/[CH:33]=[C:34](\[NH2:36])/C)[CH3:30].[CH2:38]([OH:40])[CH3:39]>>[CH2:38]([O:40][C:21]([C:20]1[CH2:23][C:33]([C:32]([O:31][CH2:29][CH3:30])=[O:37])=[CH:34][N:36]([C:4]2[CH:3]=[C:2]([CH3:7])[N:1]=[C:6]([CH2:16][N:17]3[C:18](=[O:27])[C:19]4=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]4[C:21]3=[O:22])[CH:5]=2)[CH:19]=1)=[O:22])[CH3:39]

Participants

5

Reactant 4

HCID 702EthanolHCID 142732-PyridinecarboxaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 701239Ethyl 4-(1,3-dioxoisoindolin-2-YL)-3-oxobutanoate

Product 1

HCID 705917782-Phthalimidomethyl-6-methyl-4-pyridyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 75%

Procedure

A solution of 4.7 ccs of pyridine-2-aldehyde, 12.4 g of phthalimidoacetoacetic acid ethyl ester and 5.85 g of β-aminocrotonic acid ethyl ester in 100 ccs of ethanol is heated under reflux for 24 hours and, after cooling and filtering, crystals (beige) of melting point 156°-158° C. are obtained, yield: 75%.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureafter cooling
  3. filtrationfiltering
  4. customcrystals (beige) of melting point 156°-158° C. are obtained

Sources & evidence

ORD record
ord-7a40f5b2a7284e68b6010bd61890c6d8
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Linked notes

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