N-(4-Cyano-2-fluorophenyl)methanesulfonamide → N-(4-(aminomethyl)-2-fluorophenyl)methanesulfonamide

HRID 2402314Notes

Reaction equation

HRID 2402314 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([F:14])[CH:4]=1)#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([F:14])[CH:4]=1

Participants

4

Reactant 1

HCID 15981202N-(4-Cyano-2-fluorophenyl)methanesulfonamide

Product 1

HCID 21097526N-(4-(aminomethyl)-2-fluorophenyl)methanesulfonamideYield 100.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of Example 10B (3.40 g, 16.0 mmol) and nickel powder (6.72 g, 114 mmol) in 7M NH3-MeOH (40 mL) in a 250 mL stainless steel pressure bottle at room temperature was stirred at 30 psi for 6 hours. The mixture was filtered through a nylon membrane (MeOH and THF wash) and the filtrate concentrated to afford the title compound (3.5 g), which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 7.43 (t, J=8.2 Hz, 1H), 7.19 (dd, J=11.5, 1.3 Hz, 1H), 7.13 (d, J=8.3 Hz, 1H), 3.81 (s, 2H), 2.96 (s, 3H); MS (ESI) m/z 219 (M+H+).

Workup

  1. filtrationThe mixture was filtered through a nylon membrane (MeOH and THF wash)
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2b685d0a48f6409f9844ace4e006c2c2
Source dataset
uspto-grants-2014_08
Patent number
US08796328B2

Reaction notes

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