Process for the preparation of 3,4-dialkoxyanilines

Details Process for the preparation of 3,4-dialkoxyanilines Process for the preparation of 3,4-dialkoxyanilines

1976-02-20

1977-07-12

Wyman, Daniel E.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260206, 260575, C07C 9314

Patent

active

040354237

ABSTRACT:
A new process for the production of 3,4-dialkoxyanilines in which the two alkyl groups are different from each other is disclosed. The process comprises the stepwise introduction of the alkyl groups in different stages of the process by converting pyrocatechol into its monoalkyl ether, coupling said monoalkyl ether with a phenyldiazonium salt, alkylating the 3-alkoxy-4-hydroxy-azobenzene obtained to form 3,4-dialkoxyazobenzene and reductively cleaving the latter to the corresponding 3,4-dialkoxyaniline. The 3,4-dialkoxyanilines obtainable by the new process are valuable intermediates for the preparation of 4-hydroxy-6,7-dialkoxy-3-quinoline carboxylic acid esters which are excellent coccidiostats.

REFERENCES:
patent: 1564214 (1925-12-01), Derick et al.
patent: 1722417 (1929-07-01), Grether
patent: 1890430 (1932-12-01), Perkins et al.
patent: 2191040 (1940-02-01), McNally et al.
patent: 3883503 (1975-05-01), Assche et al.
Klarmann et al., "J. Amer. Chem. Soc", vol. 54, pp. 1204-1211 (1932).
Colour Index, Third Edition, vol. 4, p. 4064, C.I. 14260.

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