General Description
2′-Aminoacetanilide (2-aminoacetanilide,
o-aminoacetanilide) can be prepared by the catalytic hydrogenation of 2-nitroacetanilide using 10%Pd/C (palladium/carbon).
Synthesis
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).
References
[1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9235 - 9244
[2] Patent: US6667300, 2003, B2. Location in patent: Page column 98
[3] Chemistry - A European Journal, 2015, vol. 21, # 26, p. 9493 - 9504
[4] Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1676 - 1677
