Sodium ethoxide → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968018ノート

反応式

HRID 1968018 の反応式
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:3].[CH3:23][N:24]1[C:28]([CH:29]=O)=[N:27][CH:26]=[N:25]1.[CH3:31][CH2:32][O-:33].[Na+]>C(OCC)(=O)CC>[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8]([CH:9]2[CH:29]([C:28]3[N:24]([CH3:23])[N:25]=[CH:26][N:27]=3)[C:32](=[O:33])[C:31]3[C:16]([C:15]([O:14][CH2:13][CH3:12])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:3]

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 136242781-methyl-1H-1,2,4-triazole-5-carbaldehydeHCID 178483208HCID 178483208、化合物

生成物 1

HCID 67261276Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(1-methyl-1H-1,2,4-triazol-5-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate収率 16%

試薬・触媒・溶媒 1

HCID 7749Ethyl Propionate溶媒

反応条件

温度
45 °C

実験手順

To a solution of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (2.21 g, 7.5 mmol) and 1-methyl-1H-1,2,4-triazole-5-carbaldehyde (1.01 g, 9.16 mmol) in ethyl propionate (110 ml) was added rapidly EtONa (sodium (490 mg, 21 mmol) in 35 mL ethanol) at 40° C., then the mixture was stirred at 45° C. for 3 hr. The resulting mixture was evaporated under reduced pressure, extracted with ethyl acetate (200 mL×3), and then concentrated the extract. The crude product was purified by column chromatography (silica gel, dichloromethane:methanol=100:1 to 10:1) to obtain a green solid (510 mg, yield 16%). LC-MS (ESI) m/z: 434 (M+1)+.

後処理

  1. customThe resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (200 mL×3)
  3. concentrationconcentrated the extract
  4. customThe crude product was purified by column chromatography (silica gel, dichloromethane:methanol=100:1 to 10:1)

出典と根拠

ORDレコード
ord-1d5316549a734367b8e4b450402fb345
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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