Triethylamine → 3-Iodo-benzaldehyde O-methyl-oxime

Participants

Reaction Steps

To a stirred solution of 3-iodo benzaldehyde (1 g, 4.3 mmol) in methanol (25 ml), O-methyl hydroxyl amine hydrochloride (0.54 g, 6.5 mmol) was added followed by triethyl amine (0.9 ml, 6.5 mmol). The reaction mixture was stirred at ambient temperature for 4 hours. Reaction mixture was concentrated under vacuum; residual mass was diluted with water (50 ml) and extracted with ethyl acetate (3×30 ml). Ethyl acetate layer was washed with water (2×30 ml) followed by brine solution, dried over anhydrous sodium sulfate and evaporated to obtain 3-Iodo-benzaldehyde O-methyl-oxime (crude), which was dissolved in glacial acetic acid (10 ml), followed by addition of sodium cyanoborohydride (0.54 g, 8.6 mmol) portion wise at 15° C. The mixture was stirred for 12 hrs at room temperature. Excess acetic acid was removed by distillation. Resulting reaction mass was basified with 10% aq. NaOH solution at 10-15° C. Aqueous layer was extracted with EtOAc (3×30 ml). The combined organic layer was washed with brine (2×30 ml) and dried over sodium sulfate. Organic layer was concentrated under vacuum to give crude mass, which was purified by chromatography to afford 1 g (89% of theory) of N-(3-Iodo-benzyl)-O-methyl-hydroxylamine

Provenance & Evidence