2-Methoxybenzaldehyde → 2-Acetoxymethyl-6-methyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1449003Notes

Reaction equation

HRID 1449003 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])=O)[CH3:12].[CH2:24]([O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])[CH3:25]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[O:2][CH3:1])[C:28]([C:27]([O:26][CH2:24][CH3:25])=[O:32])=[C:29]([CH3:30])[NH:31][C:16]=1[CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:23])[CH3:12]

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 705887642-Acetoxymethyl-6-methyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.8 g of 2-methoxy-benzaldehyde, 9.4 g of γ-acetoxyacetoacetic acid ethyl ester and 6.5 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol is heated to the boil overnight and then cooled. After filtering, light yellow crystals of melting point 84°-86° C. are obtained.

Workup

  1. temperaturecooled
  2. filtrationAfter filtering
  3. customlight yellow crystals of melting point 84°-86° C. are obtained

Sources & evidence

ORD record
ord-57d7ac2d71c548669d6d80ea04963018
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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