Sulfuric Acid → 2-(3-Cyclopropylcyclobutyl)phenylamine

Participants

Reaction Steps

1.22 g (0.006 mol) 1-(2-aminophenyl)-3-cyclopropylcyclobutanol (prepared as described in Example 9) was dissolved in 40 ml of ethanol, 1.72 g sulphuric acid (96%) were added and after addition of 250 mg of 10% Pd on charcoal, the mixture was hydrogenated for 5.5 hours at room temperature. After removal of the catalyst, ethanol was distilled off in a water jet vacuum and the residue purified by flash chromatography over silica gel (eluent: hexane/ethyl acetate 5:1). Yield: 0.94 g (82% of theory) of a cis/trans mixture of 2-(3-cyclopropylcyclobutyl)phenylamine in the form of a yellow oil (MS: M+-peak of 187).

Provenance & Evidence