Ethyl Acetoacetate → Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 2379416Notes

Reaction equation

HRID 2379416 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.[NH4+:23].[OH-:24]>C(O)C>[CH3:18][C:16]1[NH:23][C:16]([CH3:18])=[C:15]([C:14]([O:20][CH2:21][CH3:22])=[O:24])[CH:10]([C:9]2[CH:12]=[CH:13][C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:7][CH:8]=2)[C:15]=1[C:14]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 14923Ammonium HydroxideHCID 7365304-(1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 10475789Diethyl 4-[4-(1H-imidazol-1-yl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 17.2 g (0.1 mol) of 4-(1H-imidazol-1-yl)benzaldehyde, 26 g (0.2 mol) of ethyl acetoacetate and 5 ml of concentrated NH4OH in absolute ethanol (25 ml) was refluxed for 6 hours. The mixture was poured into 500 ml of ice-water and the aqueous solution was extracted with methylene chloride. The organic layers were put together, dried over CaCl2 and evaporated under vacuum. The crude product was recrystallized from Et2O, giving 25.7 g (65%) of 1,4-dihydro-2,6-dimethyl-4-[4-(1H-imidazol-1-yl)phenyl]-3,5-pyridinedicarboxylic acid, diethyl ester, m.p. 231°-233° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. extractionthe aqueous solution was extracted with methylene chloride
  3. dry with materialdried over CaCl2
  4. customevaporated under vacuum
  5. customThe crude product was recrystallized from Et2O

Sources & evidence

ORD record
ord-30c38d9714954b91b75fb3cf10a5e076
Source dataset
uspto-grants-1994_11
Patent number
US05362729

Reaction notes

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