2-Methyl-5-Nitroaniline → HCID 18505064, compound

Participants

Reaction Steps

Potassium salt of 2-bromo-5-methoxybenzoic acid (23 g) and 2-methyl-5-nitroaniline (40 g) are stirred and heated at 110° C. in the presence of 50 mg of catalytic copper for 50 minutes. Next, the reaction mixture is poured on 5% solution of potassium hydroxide in water (600 ml) and cooled. The formed precipitate is filtered off, washed with water, and the collected solutions are acidified with hydrochloric acid to pH 5. The formed solid is filtered off and crystallized from methanol-acetone (2:1) to give N-(2′-methyl-5′-nitrophenyl)-5-methoxyanthranilic acid (11.2 g, 56% yield), m.p. 219-221° C. 1H NMR (d6 DMSO): δ9.20 (bs, 1H), 7.88 (d, 1 H, J=1.9 Hz), 7.65 (dd, 1 H, J1=7.8 Hz, J2=1.9 Hz), 7.44 (d, 1 H, J=8.3 Hz), 7.43 (d, 1 H, J=2.9 Hz), 7.26 (d, 1 H, J=8.8 Hz), 7.19 (dd, 1H, J1=8.8 Hz, J2=2.9 Hz), 3.68 (s, 3 H), 2.27 (s, 3 H).

Provenance & Evidence