3,4-Dimethylaniline → HCID 62682340, compound

Participants

Reaction Steps

A solution of 3-fluoro-4-nitrobenzoic acid (2 g), 3,4-dimethylaniline (1.25 g), BOP (5.45 g) and DIEA (2.69 mL) in DMF (20 mL) was stirred at room temperature for 20 h. Then 1N NaOH aqueous solution was added (pH˜12). The aqueous layer was extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was washed with CH2Cl2/MeOH mixture, and the solid was filtered to give N-(3,4-dimethyl-phenyl)-3-fluoro-4-nitrobenzamide as a yellow solid: MS (m/z) 289 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 10.39 (s, 1H), 8.30 (t, 1H), 8.10 (d, 1H), 7.97 (d, 1H), 7.53 (s, 1H), 7.49 (d, 1H), 7.13 (d, 1H), 2.23 (s, 3H), 2.20 (s, 3H).

Provenance & Evidence