5-Morpholino-2-nitrobenzaldehyde → (5-Morpholin-4-YL-2-nitro-phenyl)-methanol

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Reaction Steps

To a suspension of the crude 5-morpholino-2-nitrobenzaldehyde in a mixture of tetrahydrofuran and ethanol (100 mL/100 mL) was slowly added sodium borohydride (4.0 g). The mixture was stirred at room temperature for 1 hour, and then was partitioned between ether and saturated ammonium chloride. The aqueous phase was extracted with ether, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product (5-morpholino-2-nitrophenyl)methanol (8.5 g, yield 62.3%, two steps).

Provenance & Evidence