Ethanol → 2-Amino-6-bromo-3-methoxypyridine

Temperature

72.5 °C

To a heterogeneous solution of 6-bromo-3-methoxy-2-nitropyridine (32) (2.32 g, 10 mmol) in of ethanol:water (40 mL, each) were added iron powder (2.8 g, 50 mmol), followed by ammonium chloride (2.64 g, 50 mmol) at room temperature. The resulting heterogeneous mixture was then stirred at 70-75° C. for 15 minutes, filtered through celite (when hot), washed with ethanol (2×50 mL) and solvent was then removed under reduced pressure. The residue upon dilution with water afforded a solid, which was isolated by filtration to give 2-amino-6-bromo-3-methoxypyridine (33). LCMS: purity: 95%, MS (m/z): 203 (MH+).

1. filtrationfiltered through celite (when hot)
2. washwashed with ethanol (2×50 mL) and solvent
3. customwas then removed under reduced pressure
4. customThe residue upon dilution with water afforded a solid
5. customwhich was isolated by filtration

ORD record

ord-332ac70e9e6745cea7de70855345040a

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815848B2