Nitric Acid → 2-Cyclopropylaniline

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Reaction Steps

A solution of 5 g (42 mmol) of cyclopropylbenzene in 20 ml of acetic anhydride is cooled to 15° C. While keeping the temperature below 20° C., 3.7 ml of 68% nitric acid are added slowly. The reaction mixture is stirred for one hour at that temperature, hydrolysed, rendered alkaline with 2N sodium hydroxide solution and extracted twice with 100 ml of ether. The organic phase is then dried and concentrated to yield a mixture of 2-nitrocyclo-propylbenzene and 4-nitrocyclopropylbenzene. The mixture is dissolved in 15 ml of ethanol and hydrogenated at normal temperature and pressure in the presence of 50 mg of PtO2. The residue obtained after filtering off the catalyst and evaporating off the solvent is purified by chromatography on silica gel to yield the title product.

Provenance & Evidence