Methanol → 7-Nitro-1,2,3,4-tetrahydronaphthalen-1-ol

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Reaction Steps

7-Nitro-3,4-dihydro-2H-naphthalen-1-one (2.0 g, 10 mmol) was dissolved in THF (50 mL) and NaBH4 (0.95 g, 25 mmol) was added. MeOH (50 mL) was then added dropwise over 5 minutes and the reaction mixture was stirred for one hour. Saturated ammonium chloride was then added to the reaction mixture, and the resulting mixture was extracted three times with ethyl acetate. The organic solutions were combined and washed with brine, dried (Na2SO4) and concentrated to give 7-nitro-1,2,3,4-tetrahydronaphthalen-1-ol. Yield 1.83 g (95%). LCMS (ESI): calc. C10H11NO3=193; obs. M+H=194.

Provenance & Evidence