(4-Nitrophenyl)methanesulfonamide → 1-(4-Aminophenyl)methanesulfonamide

4-Nitrophenylmethanesulfonamide (5.0 g, 23.1 mmol) was suspended in 90% of acetic acid and hydrogenated in the presence of palladium-carbon at ordinary temperature under normal pressure. The resulting reaction mixture was filtered to remove the catalyst and the filtrate was concentrated to dryness to give 4.3 g of 4-aminophenylmethanesulfonamide. This product was added to a mixture comprising 40 ml of water and 4.1 ml of concentrated hydrochloric acid. The obtained mixture was stirred, followed by the dropwise addition of a saturated aqueous solution of 1.63 g (23.6 mmol) of sodium nitrite at 0° C. or below. The reaction mixture was added to an acetic acid solution saturated with sulfur dioxide (prepared by saturating 30 ml of acetic acid with sulfur dioxide and adding 0.97 g of cupric chloride dihydrate to the resulting solution) under cooling with ice and stirring. The resulting mixture was stirred at room temperature for 40 minutes and poured onto ice-water. The obtained mixture was saturated with common salt and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated to dryness to give 1.7 g of the title compound.

1. customThe resulting reaction mixture
2. filtrationwas filtered
3. customto remove the catalyst
4. concentrationthe filtrate was concentrated to dryness

ORD record

ord-5c6fc72f4d494130a002505609763386

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05721246