N-[3-Cyano-4-(ethanesulfonyl)phenyl]acetamide → N-(3-(Aminomethyl)-4-(ethylsulfonyl)phenyl)acetamide

HRID 1667588Notes

Reaction equation

HRID 1667588 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])#[N:2]>CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[S:9]([CH2:12][CH3:13])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 57448183N-[3-Cyano-4-(ethanesulfonyl)phenyl]acetamide

Product 1

HCID 57448184N-(3-(Aminomethyl)-4-(ethylsulfonyl)phenyl)acetamideYield 93.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To 5C (423 mg, 1.65 mmol) in MeOH (17 mL), Raney Ni (cat) was added. The mixture was stirred under hydrogen (60 psi) for 8 h, then filtered and concentrated to provide 5D (397 mg, 92%). LC-MS: 253.23 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8077cd3d37524dee9a4260f1c487a12c
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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