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

HRID 1449010

Reaction equation

HRID 1449010 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([O:12][C:13](=[O:29])[CH2:14][C:15]([CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=O)[CH3:11].[CH2:30]([O:32][C:33](=[O:38])/[CH:34]=[C:35](\[NH2:37])/[CH3:36])[CH3:31]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])[C:34]([C:33]([O:32][CH2:30][CH3:31])=[O:38])=[C:35]([CH3:36])[NH:37][C:15]=1[CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[O:29])[CH3:11]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 701239Ethyl 4-(1,3-dioxoisoindolin-2-YL)-3-oxobutanoate

Product 1

HCID 705919372-Phthalimidomethyl-6-methyl-4-(2-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

28 g of 2-chlorobenzaldehyde, 56 g of phthalimidoacetoacetic acid ethyl ester and 25.8 g of β-aminocrotonic acid ethyl ester in 250 ccs of ethanol are heated to the boil under reflux for about 70 hours, the mixture is allowed to cool, whilst stirring, and, after filtering, light yellow crystals of melting point 166° C. are obtained, yield: 50%.

Workup

  1. temperatureunder reflux for about 70 hours
  2. temperatureto cool
  3. filtrationafter filtering
  4. customlight yellow crystals of melting point 166° C. are obtained

Sources & evidence

ORD record
ord-bb8b3075b26b4e1291786bc0d437e448
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Linked notes

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