Methanol → HCID 58085876, compound

Temperature

-78 °C

To a solution of 2-amino-4-fluoro-3-hydroxybenzoic acid (2.44 g, 9.7 mmol) in methanol (200 mL) was added thionyl chloride (3.8 mL, 50 mmol) at −78° C. The mixture was stirred in the boiling solvent for 17 h. The solvent was removed under reduced pressure; the residue was dissolved in methanol (200 mL). The solution was cooled to −78° C. and treated with thionyl chloride (8 mL, 100 mmol). The mixture was stirred in boiling solvent for 48 h. The solvent was removed under reduced pressure and the crude material was purified by column chromatography (silica gel, 0 to 70% ethyl acetate in hexanes) to afford methyl 2-amino-4-fluoro-3-hydroxybenzoate (1.5 g, 44%) as off-white solid. 1H NMR (300 MHz, CDCl3) δ 7.48-7.43 (m, 1H), 6.40 (t, J=9.3 Hz, 1H), 3.87 (s, 3H); MS (ESI+) m/z 186 (M+H).

1. customThe solvent was removed under reduced pressure
2. dissolutionthe residue was dissolved in methanol (200 mL)
3. stirringThe mixture was stirred
4. customfor 48 h
5. customThe solvent was removed under reduced pressure
6. customthe crude material was purified by column chromatography (silica gel, 0 to 70% ethyl acetate in hexanes)

ORD record

ord-05d52d7a71c7457ab0375c7cacfdf471

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863271B2