Ammonium → 4-chloro-5-nitropyridin-2-amine

Temperature

-33 °C

To 4-chloro-3-nitropyridine (10.0 g, 63.1 mmol) in 500 ml of liquid ammonium was added potassium permanganate (19.9 g, 126.1 mmol). The reaction was stirred at this temperature (−33° C.) for 5 hours then slowly warmed to room temperature. After evaporation of ammonia, water (1 L) was added. The solid formed was collected by filtration and washed with water (2 L). The solid was extracted with 1:1=DCM:EtOAc (5×500 ml). The solvent was removed and the resulting solid was recrystallized from EtOAc (400 ml) to give the title compound as a yellow solid (4.4 g, 33%). 1H NMR (400 MHz) 8.88 (s, 1H), 7.65 (b, 2H), 6.62 (s, 1H).

1. temperaturethen slowly warmed to room temperature
2. customAfter evaporation of ammonia, water (1 L)
3. additionwas added
4. customThe solid formed
5. filtrationwas collected by filtration
6. washwashed with water (2 L)
7. extractionThe solid was extracted with 1:1=DCM
8. customThe solvent was removed
9. customthe resulting solid was recrystallized from EtOAc (400 ml)

ORD record

ord-f314c4d3a1274939b9a1d826fc6afd81

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129403B2