Phosgene → 5-Isocyanatoisoquinoline

Participants

Reaction Steps

A solution of phosgene (20% in toluene, 2.9 mL, 5.5 mmol) in dichloromethane (30 mL) at 0° C. was treated with dropwise addition of 4-dimethylaminopyridine (1.43 g, 11.7 ml) in dichloromethane (15 mL). A thick white suspension formed. A solution of 5-aminoisoquinoline in 15 mL of dichloromethane was then added dropwise to this suspension. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. At the end of this time, a solution formed, and the solvent was removed under reduced pressure. The residue was titurated with 50 mL of diethyl ether to give an approximately 0.1 M solution of 5-isocyanato-isoquinoline.

Provenance & Evidence