Sodium Carbonate → 5-Bromo-2-methylpyridin-4-amine

Temperature

90 °C

To a solution of 5-bromo-2-methyl-4-nitropyridine 1-oxide (2.54 g, 10.9 mmol, 1 eq) in 10 mL concentrated hydrochloric acid was added tin chloride dihydrate (9.96 g, 43.8 mmol, 4.01 eq). The reaction mixture was stirred at 90° C. for 24 hours, and then additional tin chloride dihydrate (3.15 g, 13.8 mmol, 1.27 eq) and 5 mL concentrated hydrochloric acid was added. The reaction mixture was kept at 90° C. for an additional 24 hours, and then cooled to room temperature and adjusted to neutral pH with 2 M aqueous sodium carbonate. The solution was extract three times with dichloromethane, and the combined organic extracts dried over magnesium sulfate and concentrated to give 5-bromo-2-methylpyridin-4-amine LCMS (ESI) m+H=187.2; 1H NMR (400 MHz, DMSO-d6) δ: 8.07 (s, 1H), 6.51 (s, 1H), 6.13 (s, 2H), 2.22 (s, 3H).

1. waitThe reaction mixture was kept at 90° C. for an additional 24 hours
2. temperaturecooled to room temperature
3. extractionThe solution was extract three times with dichloromethane
4. dry with materialthe combined organic extracts dried over magnesium sulfate
5. concentrationconcentrated

ORD record

ord-cf5fea9de3984e4b880f46d09af5a389

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999998B2