Ammonia → 1-[4-(Ethylsulfonyl)phenyl]methanamine

HRID 911284Notes

Reaction equation

HRID 911284 reaction equation
[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].N>CO.[Ni]>[CH2:1]([S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 230606754-(Ethanesulfonyl)benzonitrile

Product 1

HCID 179666261-[4-(Ethylsulfonyl)phenyl]methanamineYield 43%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Combine 4-ethanesulfonyl-benzonitrile (0.7 g, 3.5 mmol), Raney® 3201 nickel (slurry in water, 0.1 g), 2N ammonia in methanol (20 mL) and hydrogenate at 50 psi for 17 h. Filter the reaction mixture through a pad of Celite® and concentrate in vacuo. Purify by SCX chromatography to obtain the title compound as a yellow oil (0.3 g, 43%).

Workup

  1. filtrationFilter the reaction mixture through a pad of Celite®
  2. concentrationconcentrate in vacuo
  3. customPurify by SCX chromatography

Sources & evidence

ORD record
ord-2215dedf08454c0d946fda742925142e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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