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

HRID 1487238Notes

Reaction equation

HRID 1487238 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].N>C(O)C.[Pd]>[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

5

Reactant 2

HCID 222AmmoniaHCID 45480189N-(2-cyanophenyl)-N-methylmethanesulfonamide

Product 1

HCID 45480190N-(2-(Aminomethyl)phenyl)-N-methylmethanesulfonamideYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-cyanophenyl)-N-methylmethanesulfonamide (16.0 g, 76 mmol) in a solution of ammonia in ethanol (500 mL, 4 mol·L−1) was added palladium on carbon (10%, 4 g). The mixture was stirred under an atmosphere of hydrogen for 24 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was washed with ether to give N-(2-(aminomethyl)phenyl)-N-methylmethanesulfonamide (14.2 g, yield 87.1%). 1H NMR (400 MHz, CDCl3) δ ppm 7.53-7.55 (m, 1H), 7.36-7.40 (m, 1H), 7.29-7.33 (m, 1H), 7.23-7.25 (m, 1H), 3.97-3.99 (br d, 2H, J=8.0 Hz), 3.27 (s, 3H), 3.00 (s, 3H). N-(2-(aminomethyl)phenyl)-N-methylmethanesulfonamide was dissolved in ether and bubbled in hydrochloride (gas) to afford the product N-(2-(aminomethyl)phenyl)-N-methylmethanesulfonamide hydrochloride (15.0 g, yield 90.4%). 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.55 (m, 1H), 7.35-7.40 (m, 1H), 7.28-7.33 (m, 1H), 7.24-7.26 (m, 1H), 3.99 (br s, 2H), 3.25 (s, 3H), 2.98 (s, 3H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. washThe residue was washed with ether

Sources & evidence

ORD record
ord-8d88cd0652cb41039b869f15ef01b101
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

Loading…