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

HRID 2379416노트

반응식

HRID 2379416 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30c38d9714954b91b75fb3cf10a5e076
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05362729

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