4-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile → [4-Methanesulfonyl-3-(trifluoromethyl)phenyl]methanamine

HRID 1364555Notes

Reaction equation

HRID 1364555 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])(=[O:4])=[O:3]>N.CO.[Ni]>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][C:6]=1[C:13]([F:14])([F:15])[F:16])(=[O:4])=[O:3]

Participants

5

Reactant 1

HCID 459337164-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile

Product 1

HCID 66632608[4-Methanesulfonyl-3-(trifluoromethyl)phenyl]methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-fluoro-3-trifluoromethylbenzonitrile (75 mg, 0.40 mmol), sodium sulfinate (44.5 mg, 0.44 mmol) in N,N-dimethylformamide (1.5 mL) was heated at 100° C. for 2 h. The reaction mixture was cooled to room temperature, quenched with water. The resulting white solid was collected via filtration, washed with cold water, dried in a vacuum oven to give 4-methanesulfonyl-3-trifluoromethyl-benzonitrile (90 mg, 90% yield). This benzonitrile was hydrogenated in 2N NH3 in methanol with 35 mg of Raney Ni under a hydrogen balloon for 2 h. The reaction mixture was filtered through a celite plug, washed with methanol, evaporated in vacuo to give the titled compound.

Workup

  1. customfor 2 h
  2. filtrationThe reaction mixture was filtered through a celite plug
  3. washwashed with methanol
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f6a0f34fb0a64f62a97a309ec3886341
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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