Methanol → 4-(Methylsulfonamido)aniline

Temperature

50 °C

N-(4-Nitro-phenyl)-methanesulfonamide (Example 3a, 25 g, 115.62 mmol) was dissolved in N,N-dimethylformamide (15 mL) with gentle heating to ˜50° C. via heat gun. Ethyl acetate (100 mL) and methanol (100 mL) were added followed by 10% palladium on carbon (4 g). The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. The mixture was stirred at 25° C. for 4.5 h. The mixture was filtered through Celite (rinsed with ethyl acetate) and concentrated in vacuo to a yellow green solution with a volume of ˜10 mL. Dichloromethane (˜50 mL) was added and a solid began to precipitate. The mixture was stirred at 25° C. for 30 min. The solid was collected by vacuum filtration and dried in vacuo to afford the desired product, N-(4-amino-phenyl)-methanesulfonamide (15.32 g, 82.26 mmol, 71% yield) as a beige powder. 1H NMR (400 MHz, DMSO-d6) δ 2.79 (3H, s), 5.00 (2H, s), 6.49 (2H, d, J=8.5 Hz), 6.87 (2H, d, J=8.6 Hz), 8.87 (1H, s).

1. temperaturevia heat gun
2. customThe mixture was degassed
3. additionthe flask was charged with hydrogen gas via balloon
4. stirringThe mixture was stirred at 25° C. for 4.5 h
5. filtrationThe mixture was filtered through Celite (rinsed with ethyl acetate)
6. concentrationconcentrated in vacuo to a yellow green solution with a volume of ˜10 mL
7. additionDichloromethane (˜50 mL) was added
8. customto precipitate
9. stirringThe mixture was stirred at 25° C. for 30 min
10. filtrationThe solid was collected by vacuum filtration
11. customdried in vacuo

ORD record

ord-e76274e365614aa192d0f4e869443ca2

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582754B2