2-Pyridinecarboxaldehyde → 2-Acetoxymethyl-6-methyl-4-(-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1449002Notes

Reaction equation

HRID 1449002 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH2:9]([O:11][C:12](=[O:21])[CH2:13][C:14]([CH2:16][O:17][C:18](=[O:20])[CH3:19])=O)[CH3:10].[CH2:22]([O:24][C:25](=[O:30])/[CH:26]=[C:27](\[NH2:29])/[CH3:28])[CH3:23]>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:26]([C:25]([O:24][CH2:22][CH3:23])=[O:30])=[C:27]([CH3:28])[NH:29][C:14]=1[CH2:16][O:17][C:18](=[O:20])[CH3:19])=[O:21])[CH3:10]

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 705905622-Acetoxymethyl-6-methyl-4-(-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.4 g of pyridine-2-aldehyde, 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, beige crystals of melting point 116° C. are obtained, yield: 60%.

Workup

  1. temperaturecooled
  2. filtrationAfter filtering
  3. custombeige crystals of melting point 116° C. are obtained

Sources & evidence

ORD record
ord-e08fa508130a4167ad5f7b53459c2441
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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