Merrell Dow Pharmaceuticals

The Dow Chemical Company

Dowelanco

Terry L Wright

Jon A Orvik

Charles D Gartner

James Sinclair

Kidisti G Mariam

Anthranilic acids substituted in the 3- and/or 5-position are valuable intermediates for the production of agricultural chemicals. These substituted anthranilic acids can be obtained in good yield without undesirable isomeric byproducts by the oxidative ring-opening of dihydroquinolin-4-ones or quinolin-2,4-diones with t-butyl hydroperoxide in the presence of a base.

Process for the preparation of 3- and/or 5-substituted anthranilic acids

Alkylthioethylamine salts are prepared by reacting certain alkenes with mercaptoethylamine salts in a glycol or glycol ether solvent in the presence of a free radical initiator. The product mixtures obtained are useful as antimicrobials as is or after the addition of inert formulation additives.

Preparation of alkylthioethylamine salts

(1H-Tetrazol-5-yl)-2(1H)-quinolones useful as antiallergic agents are described herein. The compounds are prepared by the reaction of sodium azide and ammonium chloride with an appropriate 3-cyano-2(1H)-quinolinone.

(1H-tetrazol-5-yl)-2(1H)-quinolinones and-naphthyridones and

5-Chloro-3-(substituted)-s-triazolo[4,3-a]pyridine-7-carboxylic acids useful as antiallergic agents are described herein. The compounds are prepared from an appropriate acyl 6-chloro-2-hydrazinopyridine, substituted at the 4-position with a trichloromethyl group or a cyano group, by reaction with polyphosphoric acid.

5-chloro-s-triazolo[4,3-a]-pyridine-7-carboxylic acids, useful as

(1H-Tetrazol-5-yl)thienopyridinones and related compounds which are useful as antiallergic agents are described herein. The compounds are prepared by the reaction of an appropriate cyanoketone with ammonium chloride and an azide such as sodium azide in an inert solvent such as dimethylformamide.

(Tetrazolyl) thienopyridinones

(1H-Tetrazol-5-yl)tetrazolo[1,5-a]thienopyridines and related compounds which are useful as antiallergic agents are described herein. The compounds are prepared by the reaction of an appropriate halocyano-quinoline with ammonium chloride and an azide such as sodium azide in an inert solvent such as dimethylformamide.

Tetrazolothienopyridines

Fused tetracyclic compounds containing two thiophene rings, one pyridine ring and a triazine ring and which are useful as antiallergic agents are described herein. The compounds are prepared by the reaction of an appropriate substituted aminocarboxamine with sodium nitrite in an acid such as acetic acid.

Thienotriazines

A process is described for introducing nitrile groups to compounds susceptible to Vilsmeier formylation via two sequential reactions in a single reaction medium. In the first reaction, the susceptible compound is reacted with a Vilsmeier reagent in the presence of phosphorus oxychloride. In the second reaction, a hydroxylamine salt is introduced to the medium in the presence of at least an equivalent amount of phosphorus oxychloride.

Preparation of 2-chloro-3-cyano-quinolines

(1H-Tetrazol-5-yl)tetrazolo[1,5-a]quinolines and related compounds which are useful as antiallergic agents are described herein. The compounds are prepared by the reaction of an appropriate halocyanoquinoline or isoquinoline with ammonium chloride and an azide such as sodium azide in an inert solvent such dimethylformamide.

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Antioch, CA, United States of America

Terry L Wright