Methanol → Methyl 2-amino-3-hydroxy-5-methylbenzoate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2-amino-3-hydroxy-5-methylbenzoic acid hydrobromide (2.65 g, 10.7 mmol) in anhydrous CH3OH (50 mL) was added thionyl chloride (3.9 mL, 53.4 mmol) at −78° C. The resulting reaction mixture was allowed to warm to room temperature and then heated to reflux for 17 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was treated with a saturated aqueous NaHCO3 solution to adjust pH to 7 and then extracted with EtOAc (4×100 mL). The combined organic phase was washed with H2O, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford methyl 2-amino-3-hydroxy-5-methylbenzoate (1.40 g, 72%): 1H NMR consistent.

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