Ammonium Chloride → 6-chloro-4-Methoxypyridin-3-aMine

Temperature

80 °C

A mixture of 2-chloro-4-methoxy-5-nitropyridine (208 mg, 1.10 mmol), ammonium chloride (295 mg, 5.52 mmol) and iron powder (246 mg, 4.41 mmol) in ethanol (5 mL) and water (0.5 mL) was heated at 80° C. for 18 h. The mixture was cooled and filtered through a Celite cartridge and washed through with methanol. The combined filtrate and washing was evaporated, and the residue partitioned between DCM (10 mL) and water (10 mL), the organic phase was washed further with water (10 mL), and the aqueous washes were combined and extracted with DCM (3×5 mL). The organic extracts were combined and filtered through a hydrophobic frit, and the solvent was removed by evaporation to give the product as an off-white solid (155 mg, 89%). 1H NMR (400 MHz, CDCl3): δ 7.73 (s, 1H); 6.71 (s, 1H); 3.90 (s, 3H); 3.71 (s, 2H).

1. temperatureThe mixture was cooled
2. filtrationfiltered through a Celite cartridge
3. washwashed through with methanol
4. washThe combined filtrate and washing
5. customwas evaporated
6. customthe residue partitioned between DCM (10 mL) and water (10 mL)
7. washthe organic phase was washed further with water (10 mL)
8. extractionextracted with DCM (3×5 mL)
9. filtrationfiltered through a hydrophobic frit
10. customthe solvent was removed by evaporation

ORD record

ord-c9b3ee457ec0452e8162a647df6dbe83

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791130B2