Thioanisole → HCID 23498073, compound

Participants

Reaction Steps

A mixture of 6-benzyloxy-4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile (512 mg, 1.39 mmol) and 0.9 mL of thioanisole in 7.5 mL of trifluoroacetic acid is heated at reflux for 3 hours then concentrated in vacuo. The residue is treated with ice water and then basified to pH 9-10 by the addition of aqueous ammonium hydroxide. The resultant suspension is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Trituration with diethyl ether provides 302 mg of 4-chloro-6-hydroxy-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 174-175° C.

Provenance & Evidence