Phosphorus oxychloride → 4-Chloro-8-methoxyquinoline

Participants

Reaction Steps

Compound 16 (2.65 g, 15.1 mmol) was dissolved in POCl3 (4.2 ml, 45.3 mmol) under nitrogen atmosphere and refluxed for 2 h. It was then cooled and concentrated under vacuum. The solid concentrate was taken in a beaker with 200 ml water neutralized with NaHCO3 powder and extracted with EtOAc. The solution was dried over Na2SO4, filtered, and concentrated. This crude product was then purified through column chromatography using ethyl acetate to get 17 as brown solid (2.113 g, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 4.079 (s, 3H), 7.08-7.1 (d, 1H, J=8 Hz), 7.49-7.56 (m, 2H), 7.76-7.78 (d, 1H, J=8 Hz), 8.76-8.77 (d, 1H, J=4 Hz).

Provenance & Evidence