Methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoate → Phthalimidoamlodipine

HRID 394821

Reaction equation

HRID 394821 reaction equation
[NH2:1]/[C:2](/[CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH:27]=[C:28]([C:33]([CH3:35])=O)[C:29]([O:31][CH3:32])=[O:30]>C(O)C>[Cl:24][C:25]1[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=1[CH:27]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:33]([CH3:35])[NH:1][C:2]([CH2:9][O:10][CH2:11][CH2:12][N:13]2[C:14](=[O:23])[C:15]3=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]3[C:17]2=[O:18])=[C:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 299600Methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoateHCID 11174576HCID 11174576, compound

Product 1

HCID 9871958PhthalimidoamlodipineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

24.0 g (75.4 mmoles) of ethyl 3-amino-4-(2-(phthalimido)ethoxy)crotonate and 18.9 g (79.2 mmoles) of methyl 2-(2-chlorobenzylidene)acetoacetate in 64 ml of ethanol were heated under reflux for 20 hours. The reaction mixture was diluted with 56 ml of ethanol and was cooled to crystallise the product. 14.2 g (yield 70%) of 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-(2-phthalimidoethoxy)methyl-1,4-dihydropyridine were obtained.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperaturewas cooled
  3. customto crystallise the product

Sources & evidence

ORD record
ord-3435c4404c6640cf91f4a87b281daaab
Source dataset
uspto-grants-2003_08
Patent number
US06603006B2

Linked notes

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