Acetic Acid → 6-(Methanesulfonyl)pyridin-3-amine

3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL). Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture. The mixture, which resulted, was heated to reflux for 2 h. The reaction was monitored by TLC (EtOAc/hexane, 1/1). The reaction mixture was then cooled to rt and a saturated solution of NaHCO3 (100 mL) was added to the mixture. Ethyl acetate (200 mL) was added to the above mixture and the mixture which resulted was stirred at rt for 30 min. The mixture was filtered through celite and the organic layer was collectd. The aqueous layer was extracted with ethyl acetate (200 mL×3). The organic extractions were combined and dried (NaSO4). The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6 g, 70.5%).

1. customThe mixture, which resulted
2. temperaturewas heated
3. temperatureto reflux for 2 h
4. customthe mixture which resulted
5. filtrationThe mixture was filtered through celite
6. extractionThe aqueous layer was extracted with ethyl acetate (200 mL×3)
7. extractionThe organic extractions
8. dry with materialdried (NaSO4)
9. customThe solvent was removed under reduced pressure

ORD record

ord-feb5a82fa893427bb914bfbfdbdfdb51

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06649636B1