1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)-2-(4-nitrophenyl)ethanone → 2-(4-aminophenyl)-1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13](=[O:24])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[CH2:7][CH2:6]2.[H][H]>C(O)C.[C].[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:13]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=3[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:9]2)=[O:24])=[CH:16][CH:17]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The crude product of 1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)-2 -(4-nitrophenyl)ethanone obtained in Example 7-50 was dissolved in ethanol (4 ml), and 10% palladium-carbon catalyst (38 mg) was added to this solution. The reaction mixture was stirred in a stream of hydrogen for 3 hours, and then filtered. The solvent was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/2) to give 2-(4-aminophenyl)-1-(6-methoxy-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)ethanone (159 mg, 89% in 2 steps) as a colorless oil.
Workup
- filtrationfiltered
- concentrationThe solvent was concentrated under reduced pressure
- customThe obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/2)
Sources & evidence
- ORD record
- ord-52d54eef9a21453ab758d68ad6a5e441
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06017919
Reaction notes
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