Ammonia → 3-(aminomethyl)-6-methoxy-4-phenylisoquinolin-1(2H)-one

HRID 639874Notes

Reaction equation

HRID 639874 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7]([C:14]#[N:15])=[C:6]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N>C(O)C.CO.[Ni]>[NH2:15][CH2:14][C:7]1[NH:8][C:9](=[O:13])[C:10]2[C:5]([C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2

Participants

6

Reactant 2

HCID 222AmmoniaHCID 112428516-Methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile

Product 1

HCID 685180883-(aminomethyl)-6-methoxy-4-phenylisoquinolin-1(2H)-oneYield 87.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile (200 mg) in 40 mL ethanol were added Raney Ni and 4 mL of 2 M ammonia in methanol. The reaction was shaken under 50 psi H2 pressure overnight. The reaction was filtered and concentrated to give 178 mg of 3-(aminomethyl)-6-methoxy-4-phenylisoquinolin-1(2H)-one.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c4d84084a62a419586bf8a714d351940
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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