5'-Nitro-spiro(cyclopentane-1,1'-indan)-3'-one → 5'-Amino-spiro(cyclopentane-1,1'-indan)-3'-one

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Reaction Steps

A solution of 5'-nitro-spiro(cyclopentane-1,1'-indan)-3'-one (23.1 g; 0.1 mole) in methanol (250 ml) is hydrogenated in a shaking autoclave at about 4 atg with a Raney-nickel catalyst at 40°-60° C. The mixture is chilled, the catalyst filtered off and washed with methanol, after which the filtrate is evaporated to dryness. A light yellow powder is obtained (19.5 g; yield 97%). Said powder is dissolved in 2 N hydrochloric acid and extracted with ether, and then the aqueous phase is neutralized with 2 N sodium hydroxid solution. The precipitate is filtered off, washed with water and dried, and 18.8 g of a yellow-white crystal powder is obtained. A sample is recrystallized twice from benzene and then melts at 125° C.

Provenance & Evidence