Sodium Hydroxide → 2-Chloro-6-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-methoxy-1H-quinolin-2-one of Step B (5.136 g, 29.2 mmol) in toluene (100 mL) is treated with phosphorous oxychloride 913.8 mL) and heated at 95° C. under nitrogen for 2 hours. The crude mixture is poured into ice water and basified with 50% aqueous sodium hydroxide. The solution is extracted with ethyl acetate, the extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is pre-absorbed on silica gel Merck-60 and flash chromatographed using a gradient of ethyl acetate (10–20%) in hexane to provide the title compound (5.25 g) as a white crystalline solid, m.p. 105–107° C.

Provenance & Evidence