PURPOSE: To obtain the subject compound useful as a synthetic raw material for azo dye, etc., under mild condition in a short time by reacting an N- substituted aniline compound with an organic halide in he presence of a phosphoric acid salt as an acid acceptor and an inorganic iodide compound as a catalyst.
CONSTITUTION: The objective compound of formula III can be produced by reacting an N-substituted aniline compound of formula I (R is H, Cl, No2, 1-6C alkyl, alkyloxy, alkenyl, etc.; R1 is 1-6C alkyl or alkenyl) with an organic halide compound of formula II (R2 is organic substituent; X is Cl or Br) (e.g. methyl chloride or methoxyethyl bromide) at 60-160°C (preferably 90-110°C) under a pressure of ≤5kg/cm2G (preferably 2-4kg/cm2G) in the presence of a phosphoric acid salt as an acid acceptor and an inorganic iodide compound as a catalyst. The iodide compound is e.g. NaI and its amount is preferably 0.03-0.2mol per 1mol of the compound of formula I.
INAGI TOSHIAKI
MIZUTANI TAKAYUKI
