2-Amino-4-methylbenzoic acid

Light cream solid

Toasolutionof2-nitro-4-methylbenzoicacid(500mg, 2.76mmol)inEtOH(5.50mL) was added 10percent palladium on charcoal (8percent w/w). The reaction mixture wassequentiallyevacuatedandpurgedwithhydrogenthreetimesthenstirredunderhydrogenat approximately atmospheric pressure and room temperature. The reaction wasmonitored by TLC and upon completion the catalyst was filtered off through a pad ofCeliteTM.Thesolventwasremovedinvacuotogive2-amino-4-methylbenzamide(416mg, 2.75mmol, quant.)asawhiteamorphoussolid;mp181–183°C, lit.177–179°C.a. Aniline (0.18 g, 2 mmol) was added into a solution of 2-acetylamino-4-methylbenzoic acid (0.19 g, 1 mmol) in toluene(10 mL) at room temperature. The mixture was stirred and refluxed for 10 h at 110°C. The solvent was evaporated under reduced pressure. The mixture was separated by column chromatography to give 2-amino-4-methylbenzoic acid (3, 0.10 g)and N-acetylaniline (4, 0.12 g). 2-Amino-4-methylbenzoic acid (3)16: Mp: 188.2–189.6°C.1H NMR (400 MHz, CDCl3) δ 7.81(d, J = 8.0Hz), 6.51–6.48(m, 2H), 2.28(s, 3H). Its 1H NMR data and melting point were consistent with those of standard sample.N-acetylaniline (4)17: Mp: 117.8–118.8°C. 1H NMR(400 MHz, CDCl3) δ 7.65 (br, 1H, NH), 7.50(d, 2H, J =8.0Hz), 7.30(t, 2H, J = 8.0Hz), 7.09(t, 1H, J = 7.4Hz), 2.15(s, 3H). Its 1H NMR data and melting point were consistent with those of standard sample.

Molecular Weight:151.16
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:151.063328530
Monoisotopic Mass:151.063328530
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes