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Preparation of Aniline
Hydrochloric acid (10 molL-1, 50 mL) was added over 30 min to a warmed mixture of tin
(25.0 g, 0.21 mol) and nitrobenzene (13.0 g, 0.11 mol) and the solution was mixed by swirling
and shaking. After all the acid had been added the reaction mixture was heated for 30 min, then
cooled, prompting formation of a crystalline precipitate. The reaction mixture was made alkaline by
slow addition of a cold solution of sodium hydroxide (40.0 g, 1.0 mol) in water (100 mL) with
swirling and cooling. The aqueous solution was extracted with ether (1 x 100 mL, 2 x 50 mL).
The combined ether extracts were dried over anhydrous sodium sulfate, and the solvent was
removed to give crude aniline as a dark brown liquid. Distillation of the crude product afforded pure
aniline as a pale yellow oil (5.8 g, 60%; b.p. 179-181°C).