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

HRID 1449019Notes

Reaction equation

HRID 1449019 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 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13 g of 2-chlorobenzaldehyde, 28 g of phthalimidoacetoacetic acid ethyl ester and 13 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 174°-176° C. are obtained; yield: 90%.

Workup

  1. temperatureunder reflux for about 70 hours
  2. temperatureto cool
  3. filtrationafter filtering
  4. customlight yellow crystals of melting point 174°-176° C. are obtained

Sources & evidence

ORD record
ord-0eb2b71f7960459682edac5af6a2356a
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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