2'-AMINOACETANILIDE

• 2-Methylbenzimidazole.
• N-(2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)phenyl)-5-methylfuran-2-carboxamide, a potent cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor.
• Azobenzothiazole dyes, N-[2-(6-nitrobenzothiazol-2-ylazo)phenyl]acetamide and N-[2-(benzothiazol-2-ylazo)phenyl]acetamide.

552-32-9

34801-09-7

The general procedure for the synthesis of 2'-aminoacetanilide from 2-nitroacetanilide was as follows: first, 2-nitroacetanilide (1.0 g, 5.6 mmol) was dissolved in ethanol (EtOH) and the solution was purged with nitrogen to remove oxygen. Subsequently, palladium hydroxide (Pd(OH)2, 20% by weight, carbon carrier, 200 mg) was added to the solution as a catalyst. The reaction mixture was shaken under hydrogen (H2, 20 psi) atmosphere for 2 hours. Upon completion of the reaction, it was filtered through a 0.22 μm cellulose acetate membrane (Corning) to remove the catalyst. The filtrate was concentrated under vacuum to afford the white crystalline solid product 2'-aminoacetanilide (800 mg, 96% yield). The structure of the product was confirmed by 1H NMR (300 MHz, d6-DMSO) and LRMS (ES pos.): 1H NMR δ: 9.12 (s, 1H), 7.14 (dd, J = 7.8,1.3 Hz, 1H), 6.88 (dt, J = 7.6,1.5 Hz, 1H), 6.70 (dd, J = 8.0,1.3 Hz, 1H), 6.52 (dt, J = 7.5,1.4 Hz, 1H), 4.85 (br s, 2H), 2.03 (s, 3H); LRMS (ES pos.) m/z = 151 (M + 1).