Nitric Acid → 8-Nitro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one

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Reaction Steps

65% Nitric acid (0.33 ml) is mixed at 0° C. with 96% sulfuric acid (0.44 ml). To this end, a solution of 1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one (1.9 g, 5.3 mmol) in dichloromethane (5 ml) is added in drops. After 1 hour at room temperature, the batch is poured onto ice water, the solid is filtered off and washed with water. Column-chromatographic purification (SiO2) of the filter residue with ethyl acetate-hexane yields 0.65 g (53%) of product.

Provenance & Evidence