N-(3-Cyano-phenyl)-4-methoxy-N-methyl-benzamide → N-(3-Aminomethyl-phenyl)-4-methoxy-N-methyl-benzamide

HRID 578719Notes

Reaction equation

HRID 578719 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:20])[C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]>N.CO.C1COCC1.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([N:9]([CH3:20])[C:10](=[O:19])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 1

HCID 47407961N-(3-Cyano-phenyl)-4-methoxy-N-methyl-benzamide

Product 1

HCID 62970261N-(3-Aminomethyl-phenyl)-4-methoxy-N-methyl-benzamide

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

450 mg (1.7 mmol) N-(3-Cyano-phenyl)-4-methoxy-N-methyl-benzamide were dissolved in 10 ml NH3 in methanol (10%) and 10 ml THF. 500 mg Sponge nickel catalyst were added and the mixture was hydrogenated for 14 h at 5 bar pressure. The mixture was filtered and the filtrate was evaporated.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d08239081437489692c11e30e0e768c2
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

Loading…