Preparation of ortho-methyl anilines from ortho-amino benzyl sul

Details Preparation of ortho-methyl anilines from ortho-amino benzyl sul Preparation of ortho-methyl anilines from ortho-amino benzyl sul

1985-02-13

1988-10-11

Hines, Robert V.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564102, 564282, 564440, 558412, 558418, 560 19, C07C 8750

Patent

active

047772921

ABSTRACT:
This invention relates, in one of its aspects, to a process for the preparation of ortho-methyl anilines from ortho-amino benzyl sulfoxides. An ortho-amino benzyl sulfoxide is converted to an ortho-amino benzyl halide by reaction with a nonoxidizing acid halide and is converted to a stable quaternary salt by reaction with a tertiary amine in the presence of an alcohol. The quaternary salt may be cleaved by hydrogenation to form ortho-methyl anilines. Other aspects of the invention relate to novel intermediate quaternary salts and to a process for forming those quartenary salts.

REFERENCES:
patent: 4480130 (1984-10-01), Ku
patent: 4496765 (1985-01-01), Ku et al.
Adams et al., "Organic Reactions", vol. 7, pp. 277-280 (1953).
Grossman et al., "Tetrahedron Letters", vol. 6, pp. 497-500 (1922).

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