2-Iodobenzoic acid → N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

Participants

Reaction Steps

To a solution of 4.84 grams of potassium carbonate in 18 ml. of water were added in succession 8.0 grams of o-iodobenzoic acid, 3.88 grams of 5-amino-1,3-dimethyl pyrazole and 0.8 gram of the copper catalyst. The mixture was stirred at reflux for 5 hours. There was then added an additional 50 milliliters of water, the mixture being refluxed an additional 30 minutes and then filtered through diatomaceous earth. The filtrate was digested with decolorizing carbon, heated to reflux and filtered. The filtrate was cooled and acidified with 3N aqueous hydrochloric acid to produce N-(1,3-dimethyl-5-pyrazolyl)anthanilic acid, mp 175°-189° C., recrystallized from ethanol to give needles, mp 204°-206° C.

Provenance & Evidence