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Two layers are then obtained, one of 20% sodium chloride solution and the other of aniline. Finally, pure aniline may be obtained by distillation. The yield in this process is nearly quantitative. Particular care must be taken in handling aniline as it is poisonous ; the first symptom is cyanosis, the lips, for example, appearing bluish. Fe; 30% HC1 Heat Nitrobenzene f^f) Na2C03 (^ i. Anilinium chloride Aniline Aniline is also prepared industrially by amination of chlorobenzene with ammonia in the presence of a copper oxide catalyst and at high temperature and pressure.

The Curtius reaction involves the preparation of the azide from the appropriate carboxylic acid as starting material and involves rearrangement as one of its steps. NaN 3 RC0 2 H > RCOC1 > RCON3 + NaCl Carboxylic acid Acid chloride Acid azide\ 1 RC0 2 CH 3 Ester NH 2 NH 2 >RCONHNH2+CH3OH Acid hydrazide RN=C=0->RNH 2 + C 0 2 Isocyanate Amine I HONO RCON3 + H 2 0 The required acid azide may be obtained from the acid chloride and sodium azide or alternatively from an acid hydrazide by treatment with nitrous acid at a low temperature.

HOJH RNHCO'NHCOR —=—« RNH — C — O — H + RCONH, A carbamic acid RNH, +CO, However, under the conditions of the hydrolysis, in the presence of excess hypobromite OBr, the amine formed is oxidized to the corresponding cyanide: RCH 2 NH 2 2ÔBr > RC=N + 2Br-+2H 2 0 PROPERTIES, PREPARATION AND REACTIONS 49 For this reason the Hofmann rearrangement on higher aliphatic amides is carried out in methanolic solution. Under these conditions, the alcohol adds to the isocyanate at a faster rate than does the haloamide salt and the urethans are obtained.

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