Preparation of 2-chloro-4-methoxy-5-nitro-toluene and 2-chloro-4-methoxy-5-aminotoluene

Abstract

Abstract 5-Nitro-4-alkoxy-2-chlorotoluene, wherein the alkoxy group contains 1 to 2 carbon atoms, is prepared by reacting 5-nitro-2,4-dichlorotoluene with the desired alkali metal alcoholate in the presence of the corresponding alcohol at a temperature from 65 DEG to 80 DEG C., the amount of said alcoholate not exceeding 1.1 mol. per mol. of 5-nitro-2,4-dichlorotoluene. In the preferred method, equimolecular quantities of reactants are used. The resulting compound may be reduced to the corresponding 5-amino-4-alkoxy-2-chlorotoluene, e.g. with acetic acid and zinc. The Specification also states that 5-amino-4-methoxy-2-chlorotoluene has been prepared by acylating 2-methoxy-5-methylaniline, e.g. introducing the acetyl or oxalyl radical, chlorinating the resulting acylated compound and hydrolysis of the acylamino group in the resulting 5-acylamino - 4 - methoxy - 2 - chlorotoluene. 5-Nitro-2,4-dimethoxytoluene by heating 5-nitro-2,4-dichlorotoluene with sodium methylate in methanol at 115/120 DEG C., the amount of alcoholate being approximately 2 mols. per mol. of dichlorotoluene. 5-Nitro-2,4-dichlorotoluene by the action of concentrated sulphuric and nitric acids on 2,4-dichlorotoluene. 5 - Nitro - 1 - chloro - 2 : 4 - dimethoxy benzene is obtained by heating 5-nitro-1,2,4-trichlorobenzene and approximately two mols. of sodium methylate in methanol.

Inventors

• 👤 Rottschaefer Bernard William

Bibliographic Details