Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-3-nitroquinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-benzyloxy-3-nitroquinolin-4-ol (75.0 g, 253 mmol), which was made in a separate run, in 500 mL of N,N-dimethylformamide was placed under an atmosphere of nitrogen. The suspension was treated with phosphorous oxychloride (27.8 mL, 304 mmol) dropwise over 1.5 h. After 18 h, the reaction mixture was cooled to 0° C. and then poured into 1 L of ice water. The mixture was stirred until the ice had melted. A tan/yellow precipitate was collected by vacuum filtration. The solid was dissolved in dichloromethane (500 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 71.7 g of 7-benzyloxy-4-chloro-3-nitro-quinoline as an orange solid.

Provenance & Evidence