2-Amino-3,4-dimethylbenzoic acid

White to yellow solid

General procedure: The starting material 2-amino-5-methoxy-3, 4-dimethyl-benzoic acid8c was synthesized according to a method previously reported in theliterature.[25] To a magnetically stirred solution of 2-(2-bromophenyl)acetic acid 7a (0.61g, 2.8 mmol) and 8c (0.5g, 2.6 mmol) in DMF wasadded powdered Cu (0.02g), Cu2O (0.02g) and K2CO3 (0.28g, 2 mmol)successively. The reaction mixture was heated to 95 for 12 h. Uponremoval of the solvents, the residue was triturated with 1 N NaOHsolution. The whole mixture was filtered off and the alkaline solutionwas acidified with conc. HCl, and then collected the precipitate. Thedried residue was subjected to column purification (PE/EA 4:1) tofurnish the desired compound. A solution of 2-((2-(carboxymethyl)phenyl) amino)-5-methoxy-3, 4-dimethyl-benzoic acid in Eaton's reagent(P2O5 -CH3SO3H) (5 ml) at room temperature was heated to90 C for 1 h. After cooling to room temperature, the mixture was addedslowly to the saturated aqueous NaHCO3 solution. The crude was accumulatedby filtration followed by purification with silica gel columnchromatography to give 0.3g product: the dark brown solid, yield 37.5%. 1H NMR (400 MHz, CHLOROFORM-D) delta (ppm): 8.17 (d, J = 8.0 Hz, 1H), 7.81 (s, 1H), 7.62 (dd, J = 7.1, 0.9 Hz, 1H), 7.42 -7.36 (m, 1H), 3.99 (s, 3H), 3.92 (s, 2H), 2.39 (s, 3H), 2.37 (s, 3H). 13CNMR (101 MHz, DMSO-D 6) delta (ppm): 173.51, 161.50, 155.21, 153.01, 139.05, 134.15, 132.91, 125.57, 124.99, 122.86, 121.12, 120.42, 119.14, 101.45, 55.73, 38.54, 13.16, 13.02. HRMS (ESI) m/z [M+H] + calculated for C18H15NO3: 294.1130 found: 294.1123.General procedure: To a magnetically stirred solution of 2-(2-bromophenyl)acetic acid7a (0.72g, 3.3 mmol) and General procedure: To a magnetically stirred solution of 2-(2-bromophenyl)acetic acid7a (0.72g, 3.3 mmol) and General procedure: To a magnetically stirred solution of 2-(2-bromophenyl)acetic acid7a (0.72g, 3.3 mmol) and

Molecular Weight:165.19
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:165.078978594
Monoisotopic Mass:165.078978594
Topological Polar Surface Area:63.3
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes