Ammonia → 2,6-Dimethoxymethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1283288

Reaction equation

HRID 1283288 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][C:18]([CH2:20][O:21][CH3:22])=O)[CH3:14].[NH3:24]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]([F:12])([F:11])[F:1])[C:17]([C:16]([O:15][CH2:13][CH3:14])=[O:23])=[C:18]([CH2:20][O:21][CH3:22])[NH:24][C:18]=1[CH2:20][O:21][CH3:22])=[O:23])[CH3:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 12645099Ethyl 4-methoxy-3-oxobutanoate

Product 1

HCID 681206652,6-Dimethoxymethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.7 g of 2-trifluoromethylbenzaldehyde, 16 g of γ-methoxyacetoacetic acid ethyl ester and 5 ml of aqueous concentrated ammonia in 30 ml of ethanol are heated to the boil overnight, the mixture is cooled and 2,6-dimethoxymethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained in the form of light brown crystals of melting point 133°-134°C, in a yield of 60% of theory.

Workup

  1. temperaturethe mixture is cooled

Sources & evidence

ORD record
ord-34ec25078a594fb58e3f762a57550ec8
Source dataset
uspto-grants-1976_08
Patent number
US03974278

Linked notes

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