A mixture of
107 g. (1 mole) of methylaniline (Note
1),
145 cc. of concentrated hydrochloric acid, and 400 g. of ice is placed in a
3-l. flask equipped with a
mechanical stirrer. The mixture is stirred vigorously, and the temperature is maintained at 10° or below by the addition of more ice as required, while a solution of
70 g. (1 mole) of sodium nitrite in 250 cc. of water is added during the course of five or ten minutes. Stirring is then continued for one hour more. The oily layer is separated, and the aqueous portion is extracted with two
100-cc. portions of benzene. The
benzene is removed by distillation at ordinary pressure, and the residue is fractionated under reduced pressure. The main fraction of the
nitrosomethylaniline distils as a light yellow liquid boiling at
135–137°/13 mm. The yield (Note
1) is
118–127 g. (
87–93 per cent of the theoretical amount).