5-Nitrosalicylaldehyde → Benzaldehyde, 2-hydroxy-5-nitro-, oxime

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-5-nitrobenzaldehyde (2.10 g, 12.6 mmol) in pyridine (31.0 mL) and EtOH (5.0 mL) was added hydroxylamine hydrochloride (1.75 g, 25.2 mmol). After stirring at 20° C. for 10 h, the mixture was diluted with CH2Cl2 (125 mL) and washed with water (4×70 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and evaporated. The residue was triturated with EtOH and filtered. The resulting solid was rinsed with ether and dried under vacuum to obtain the title compound (1.86 g, 81% yield) as a yellowish solid: MS (electrospray, +ions) m/z 183 (M+H).

Provenance & Evidence