Hydroxyamine hydrochloride → Methyl 5-[(hydroxyimino)methyl]-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-formyl-2-methoxybenzoate 1.0 g, 5.15 mmol), hydroxylamine hydrochloride (1.8 g, 25.75 mmol) and sodium acetate (2.1 g, 25.75 mmol) were combined in a ethanol/water mixture (1:1, 40 mL) and stirred at 50° C. for 1 h. After cooling to room temperature, the reaction mixture was poured in to ice water and extracted with methylene chloride (2×). The combined organic layers were washed with brine (2×), dried over sodium sulfate and concentrated to afford 1.04 g (97%) which was used without purification. LC/MS (HPLC method 3): tR=1.63 min, 210.06 (MH)+.

Provenance & Evidence