3-Chlorobenzoic Acid → HCID 3011465, compound

Participants

Reaction Steps

2-Amino-4-chloropyridine (90 mg, 0.70 mmol, 1.1 eq), 3-chlorobenzoic acid (0.1 mg, 0.6 mmol, 1 eq), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (135 mg, 0.704 mmol, 1.10 eq) and 4-dimethylaminopyridine (7.8 mg, 0.064 mmol, 0.10 eq) were dissolved in CH2Cl2 (5 ml) and stirred at rt overnight. Water was added and the layers separated. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 160 mg (94%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 11.21 (s, 1H), 8.39 (d, J=5.4 Hz, 1H), 8.27 (d, J=1.6 Hz, 1H), 8.06 (t, J=1.8 Hz, 1H), 7.96 (dt, J=7.6, 1.2 Hz, 1H), 7.67 (ddd, J=8.0, 2.1, 1.0 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.32 (dd, J=5.4, 2.0 Hz, 1H); ES-MS [M+1]+: 267.1.

Provenance & Evidence