Amination/demethylation process

Details Amination/demethylation process Amination/demethylation process

1976-02-12

1980-04-15

Doll, John

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

549 68, 2603473, 2603474, 2603477, 260689, 546311, C07C 8511

Patent

active

041983505

ABSTRACT:
This invention relates to the intramolecular oxidation and reduction of aromatic hydrocarbons containing at least one methyl group and a nitro group ortho to the methyl group. Further, it relates to preparing methyl o-amino arylcarboxylates and aromatic amines. The process comprises reacting aromatic hydrocarbons having at least one methyl group and a nitro group ortho to the methyl group in a solvent at a temperature of about 450.degree. to 750.degree. C. When the solvent is methanol, methyl o-amino arylcarboxylates useful in anesthetics, printing inks for polyethylene, and useful in the manufacture of azo dyes are produced. Novel substituted methyl anthranilates have been produced which have the foregoing uses. When no solvent is used or the solvent is benzene, cyclohexane, toluene, hexafluorobenzene or any other non-reactive solvent, the compounds are demethylated and aromatic amines are produced. These aromatic amines are useful as pesticides, anti-oxidants and as pickling inhibitors for aluminum and zinc and as curing agents for epoxy resins.

REFERENCES:
patent: 2377071 (1945-05-01), Castner et al.
patent: 3293295 (1966-12-01), Swakon et al.
patent: 3504035 (1970-03-01), Polinski et al.
Fields et al., "J. Amer. Chem. Soc.", vol. 89:13, pp. 3224-3228 (1967).
Janzen, "J. Amer. Chem. Soc.", vol. 87:15, pp. 3531-3532 (1965).

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