Acetic Acid → 4-Chloro-2-{[(pyridin-3-yl)methyl]amino}benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dichlorobenzoic acid (10 g, 53 mmol), 3-aminomethylpyridine (4.5 ml, 44 mmol), K2CO3 (7.8g, 56 mmol) and CuBr (80 mg, cat) in DMF (20 ml) was heated at 150° C. for 1 hour, cooled to 0° C., diluted with water (80 ml) and carefully acidified with glacial acetic acid. The resulting solid was collected by filtration, washed with water, acetone and ether to give the pure product (>99% by HPLC) as a bluish white solid (3.46 g, 30%), m.p. 235°-236° C.; 1H NMR d (DMSO, 360 MHz, 353 K) 8.60 (bs, 1H, aromatic), 8.49 (bs, 1H, aromatic), 7.79 (d, J=8.5 Hz, 1H, aromatic), 7.72 (d, J=7.8 Hz, 1H, aromatic), 7.35 (dd, J=4.8, 7.6 Hz, 1H, aromatic), 6.74 (d, J=1.8 Hz, 1H, aromatic), 6.59 (dd, J=2.0, 8.4 Hz, 1H, aromatic), 4.51 (s, 2H, CH2); HRMS [M-2H]- calcd for C13 H9N2O2Cl: 260.0353. Found: 260.0348. Anal. calcd for C13H11ClN2O2.1/4H2O: C, 58.44; H, 4.33; N, 10.48. Found: C, 58.30; H, 4.10; N, 10.25.

Provenance & Evidence