Lithium Carbonate → 2-[(4-tert-Butylphenyl)amino]-6-chloro-3-nitrobenzoic acid

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Reaction Steps

A mixture of 2,6-dichloro-3-nitrobenzoic acid (4.72 g, 0.02 mol), 4-tertbutylaniline (4.47 g, 0.03 mol), lithium carbonate (1.48 g, 0.02 mol), and 1-propanol (10 mL) was refluxed with stirring for 20 h. The solvent was evaporated and to the residue, water (30 mL) and benzene (50 mL) were added. The mixture was made strongly basic with sodium hydroxide and stirred for 1h. Orange precipitate was collected by filtration and washed with benzene and ether. Dry precipitate was dissolved in water and acidified with diluted hydrochloric acid. Resulting precipitate was collected and crystallized from acetone-water to give 4.55 (65%) of the desired product, mp 201°-204° C. Anal. (C31H27N7O6) C, H, N.

Provenance & Evidence