Methanol → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 908019ノート

反応式

HRID 908019 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].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[O-:35][CH2:36][CH3:37].[Na+].CO>C(OCC)(=O)CC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([C:24]([F:34])([F:33])[F:23])=[CH:26][CH:27]=3)[C:13](=[O:14])[C:12]3[C:16]([C:15]([O:35][CH2:36][CH3:37])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:21][CH:22]=1)[CH3:1]

参加物

6

反応物 4

HCID 887MethanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208、化合物

生成物 1

HCID 67386466Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-(4-(trifluoromethyl)phenyl)-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
0 °C

実験手順

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (541 mg, 1.84 mmol) and 4-(trifluoromethyl)benzaldehyde (320 mg, 1.84 mmol) in anhydrous ethyl propionate (25 mL) was cooled to 0° C. Then sodium ethoxide in methanol solution (sodium (127 mg, 5.51 mmol) in anhydrous ethanol (10 mL)) was added dropwise and the mixture was stirred at 25° C. for 4 hr. The resulting mixture was quenched with water (5 mL), and then evaporated the solvents off under reduced pressure. The residue was extracted with ethyl acetate (100 mL×3) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated to give crude product, which was purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1) to give the title compound (150 mg, yield 16%) as a yellow solid. LC-MS (ESI) m/z: 497 (M+1)+.

後処理

  1. customThe resulting mixture was quenched with water (5 mL)
  2. customevaporated the solvents off under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (100 mL×3)
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1)

出典と根拠

ORDレコード
ord-8eb3c6cbe1f6471db242a029948bc130
出典データセット
uspto-grants-2011_09
特許番号
US08012976B2

反応ノート

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