Ethyl Propionate → methyl 3-(1-ethyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1967983노트

반응식

HRID 1967983 반응식
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]=O)[CH3:2].[CH:10](=[N:17]/[C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][O:21][C:22]2=[O:27])\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:28][O-:29].[Na+].C(OCC)(=O)CC>>[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]1[C:28](=[O:29])[C:19]2[C:23]([C:22]([O:21][CH3:20])=[O:27])=[CH:24][CH:25]=[CH:26][C:18]=2[NH:17][CH:10]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

참가 물질

5

반응물 4

HCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 110623771-ethyl-1H-imidazole-2-carbaldehydeHCID 178519069HCID 178519069, 화합물

생성물 1

HCID 67260994methyl 3-(1-ethyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate수율 12.1%

실험 절차

To 1-ethyl-1H-imidazole-2-carbaldehyde (520 mg, 4.19 mmol), (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (994 mg, 4.19 mmol), sodium methanolate (385 mg, 16.8 mmol) and ethyl propionate (15 mL) were added and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1). 190 mg of methyl 3-(1-ethyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate was obtained. LC-MS (ESI) m/z: 390 (M+1)+.

후처리

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1)

출처 및 근거

ORD 기록
ord-e5bfe60074bb4078b08dcce90e412d18
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420650B2

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