Water → tert-Butyl{6-chloro-3-[(hydroxyimino)methyl]pyridin-2-yl}carbamate

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Reaction Steps

15.45 g (60.2 mmol) of tert-butyl (6-chloro-3-formylpyridin-2-yl)carbamate (Example 2A) were initially charged in 750 ml of ethanol and admixed with a solution of 225 ml of water and 9.38 g (120.4 mmol) of sodium acetate and stirred for 5 min. A solution of 225 ml of water and 8.36 g (114.4 mmol) of hydroxylamine hydrochloride was added and the mixture was stirred at RT for 4 h. At 20° C., the reaction mixture was concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and washed twice with saturated sodium hydrogencarbonate solution and once with saturated sodium chloride solution. The organic phase was removed, dried over magnesium sulphate and concentrated at 20° C. on a rotary evaporator. 15.5 g (80% of theory) of the product were obtained in solid form.

Provenance & Evidence