Sodium Hydroxide → 3-(Methanesulfonylmethyl)aniline

1-Methylsulfonylmethyl-3-nitrobenzene (4.70 g, 21.8 mmol) was added ethanol (70 mL) and the mixture was heated to reflux. At reflux the mixture was added SnCl2 dihydrate (24.6 g, 109 mmol) and heating at reflux was continued for 1 hour. After cooling, the mixture was poured into ice/water (200 mL) and neutralised (to pH 7) with 1 N sodium hydroxide. The mixture was filtered through celite, and the filter cake was washed with ethyl acetate. The phases from the combined filtrate and washings were separated, and the aqueous phase was extracted with ethyl acetate (2×150 mL). The combined organic phases were dried (MgSO4) and evaporated in vacuo to afford 2.23 g (55%) 3-(methylsulfonylmethyl)aniline.

1. temperaturethe mixture was heated to reflux
2. temperatureAt reflux the mixture
3. temperatureheating
4. temperatureat reflux
5. temperatureAfter cooling
6. filtrationThe mixture was filtered through celite
7. washthe filter cake was washed with ethyl acetate
8. customThe phases from the combined filtrate and washings were separated
9. extractionthe aqueous phase was extracted with ethyl acetate (2×150 mL)
10. dry with materialThe combined organic phases were dried (MgSO4)
11. customevaporated in vacuo

ORD record

ord-3c6dc1ed73d244aea2d855b9aacf391e

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06875760B2