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

Participants

Reaction Steps

A mixture of 2-iodobenzoic acid (14.9 g, 0.06 mol), 5-amino-1,3-dimethylpyrazole (6.7 g, 0.06 mol), DMF (125 ml), Cu(OAc)2 (0,4 g) and K2CO3 (8.28 g, 0.06 mol) is refluxed overnight. The reaction mixture is poured into ice water (500 ml) and then is acidified with acetic acid to a pH of about 5. The solid that forms is collected by filtration, washed with water (100 ml) and dried. The solid is dissolved in hot CHCl3 (300 ml), filtered, dried over MgSO4 and evaporated to about 20 ml. Hexane (50 ml) is added, and then the product is collected by filtration, washed with hexane (30 ml) and dried to afford 6.2 g of N-(1,3-dimethyl-pyrazol-5-yl)anthranilic acid, m.p. 210°-211° C.

Provenance & Evidence