Thionyl Chloride → HCID 66958491, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-nitroquinolin-4-ol (8.15 g) in DCM (100 mL) was added DMF (3.33 mL) and thionyl chloride (3.47 mL) and the reaction mixture was refluxed for 2.5 h when all solids dissolved. The solution was cooled to 0° C. and a solution of (3-aminopropyl)-carbamic acid tert-butyl ester (8.3 g) and Et3N (6.5 mL) in DCM (20 mL) was added dropwise. The reaction mixture was stirred overnight then poured into saturated sodium bicarbonate solution and the product extracted using DCM. The combined organic layer were washed with brine, water, dried, filtered and the solvents evaporated. The residue was trituated with diethylether to leave the subtitle compound (13 g).

Provenance & Evidence