Water → 2-acetamido-N-(4-nitrophenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-acetamidobenzoic acid (C1) (5.30 g, 29.58 mmol) and CDI (5.75 g, 35.50 mmol, 1.2 equivalent) in N-methylpyrrolidinone (20 mL) was heated at 55-60° C. for 2 h. 4-Nitroaniline (6.13 g, 44.37 mmol, 1.5 equivalent) was then added and the mixture was heated to 140° C. for 4 h, then poured into water (400 mL) and stirred for 18 h. The resulting precipitate was filtered and washed sequentially with water and CH2Cl2 and then crystallized from MeOH to give C2 (4.84 g; 55%) as a yellow solid; mp (MeOH) 259-261° C.; 1H NMR [(CD3)2SO] δ 10.80 (s, 1 H, NH), 10.15 (s, 1 H, NH), 8.29 (m, 2 H, H-{acute over (3)}& H-{acute over (5)}), 8.12 (t, J=1.8 Hz, 1 H, H-2), 7.84 (br dd, J=8.1, 1.2 Hz, 1 H, H-6), 7.65 (td, J=7.8, 2.5 Hz, 1 H, H-4), 7.48 (t, J=7.9 Hz, 1 H, H-5), 2.08 (s, 3H, COCH3); Anal. Calc. For C15H13N3O4: C, 60.2; H, 4.4; N, 14.0; found C, 60.4; H, 4.6; N, 14.1%.

Provenance & Evidence