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

HRID 1986431Notes

Reaction equation

HRID 1986431 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a3be134007e94bdb852f70bae3dfe9cf
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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