N-(2-cyanophenyl)-N-methylmethanesulfonamide → N-(2-(Aminomethyl)phenyl)-N-methylmethanesulfonamide

HRID 472422Notes

Reaction equation

HRID 472422 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11])#[N:2].[H][H]>[Pd].N.CO>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:14])[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

6

Reactant 2

HCID 45480189N-(2-cyanophenyl)-N-methylmethanesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 45480190N-(2-(Aminomethyl)phenyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

N-(2-Aminomethyl-phenyl)-N-methyl-methanesulfonamide was prepared from N-(2-cyano-phenyl)-N-methyl-methanesulfonamide (0.75 g, 3.5 mmol) via hydrogenation using a Paar apparatus with 10% Palladium on Carbon (50% Wet)(5:45:50, palladium:carbon black:water, 0.75 g, 0.35 mmol) and hydrogen (50 psi) in 7M ammonia in methanol (50 mL). The mixture was shaken on a Paar apparatus until adsorption of hydrogen ceased. The mixture was degassed, backflushed with nitrogen, filtered through a plug of diatomaceous earth and rinsed with dichloromethane. The filtrate was evaporated under reduced pressure. Product isolated as a tan viscous oil (0.76 g, 100%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.54 (d, J=7.7 Hz, 1H), 7.38 (ddd, J=7.6, 0.9, 0.9 Hz, 1H), 7.30 (ddd, J=7.9, 1.3, 1.3 Hz, 1H), 7.24 (dd, J=7.9, 0.8 HZ, 1H), 4.00 (br s, 2H), 3.26 (s, 3H), 2.99 (s, 3H). MS=215 (MH)+.

Workup

  1. customThe mixture was degassed
  2. filtrationfiltered through a plug of diatomaceous earth
  3. washrinsed with dichloromethane
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-863ee5e2a9884aa2a803592b070a5a0a
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

Loading…