N-(6-chloro-3-iodopyridin-2-yl)pivalamide → 2-Amino-6-chloro-3-iodopyridine

Participants

Reaction Steps

A suspension of N-(6-chloro-3-iodopyridin-2-yl)-2,2-dimethyl propionamide (Preparation 108, 5.0 g, 14.8 mmol) in 1M HCl was heated to reflux for 4.5 h. The reaction was cooled to rt and then extracted with diethyl ether (2×50 mL). The organics were washed with Na2CO3 solution (2×50 mL) before being dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, CH2Cl2) afforded the title compound. δH(CDCl3): 7.76 (1H, d), 6.46 (1H, d), 5.43-5.20 (2H, br s).

Provenance & Evidence