Phosgene → 5-Isocyanatoisoquinoline

Participants

Reaction Steps

Phosgene (20 ml, 20% in toluene from Fluka) in CH2Cl2 (300 mL) at 0° C. was treated with DMAP (10 g) in CH2Cl2 (100 mL) slowly. After complete addition, the mixture was treated with 5-aminoisoquinoline (5 g) in CH2Cl2 (100 mL) dropwise. The mixture was allowed to warm to room temperature and then stirred overnight. The solvent was removed under reduced pressure. The solid residue was extracted with diethyl ether (400 mL). The diethyl ether was filtered to provide the title compound in diethyl ether as a pale yellow solution. The diethyl ether solution was used in subsequent reactions without further purification.

Provenance & Evidence