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-chlor-3-formylpyridin-2-yl)carbamate (Example 4A) were initially charged in 750 ml of ethanol, a solution of 225 ml of water and 9.38 g (120.4 mmol) of sodium acetate was added and the mixture was 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 bicarbonate solution and once with saturated sodium chloride solution. The organic phase was separated off, dried over magnesium sulfate and concentrated at 20° C. on a rotary evaporator. This gave 15.5 g (80% of theory) of the product as a solid.

Provenance & Evidence