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

HRID 1967983ノート

反応式

HRID 1967983 の反応式
[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]

参加物

5

反応物 4

HCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 110623771-ethyl-1H-imidazole-2-carbaldehydeHCID 178519069HCID 178519069、化合物

生成物 1

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

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-e5bfe60074bb4078b08dcce90e412d18
出典データセット
uspto-grants-2013_04
特許番号
US08420650B2

反応ノート

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