Ammonia → 2-{[3-(Aminomethyl)-4-phenyl-2-propylquinolin-6-yl]oxy}acetamide

HRID 1986431ノート

反応式

HRID 1986431 の反応式
[C:1]([C:3]1[C:4]([CH2:24][CH2:25][CH3:26])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH2:20][C:21]([NH2:23])=[O:22])=[CH:8][CH:7]=2)#[N:2].N.CO>[Co].O1CCCC1>[NH2:2][CH2:1][C:3]1[C:4]([CH2:24][CH2:25][CH3:26])=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][C:9]([O:19][CH2:20][C:21]([NH2:23])=[O:22])=[CH:8][CH:7]=2

参加物

6

反応物 3

HCID 222AmmoniaHCID 887MethanolHCID 688308572-[(3-Cyano-4-phenyl-2-propylquinolin-6-yl)oxy]acetamide

生成物 1

HCID 688298542-{[3-(Aminomethyl)-4-phenyl-2-propylquinolin-6-yl]oxy}acetamide収率 62%

試薬・触媒・溶媒 2

HCID 104730Cobalt触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-[(3-cyano-4-phenyl-2-propylquinolin-6-yl)oxy]acetamide (1.0 g, 2.9 mmol), Raney-cobalt (5 ml), 25% aqueous ammonia (5 ml), methanol (5 ml) and tetrahydrofuran (5 ml) was reacted under a hydrogen atmosphere at 0.5 MPa, 70° C. for 6 hrs. The reaction mixture was filtered, and water was added to the filtrate. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (0.62 g, yield 62%) as white crystals.

後処理

  1. customwas reacted under a hydrogen atmosphere at 0.5 MPa, 70° C. for 6 hrs
  2. filtrationThe reaction mixture was filtered
  3. additionwater was added to the filtrate
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a3be134007e94bdb852f70bae3dfe9cf
出典データセット
uspto-grants-2009_06
特許番号
US07547710B2

反応ノート

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