Dimethylformamide → HCID 66599159, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-quinolinecarboxylic acid (750 mg, 4.33 mmol, commercially available from e.g. Sigma-Aldrich, Acros or Apollo) and oxalyl chloride (0.417 ml, 4.76 mmol) in dichloromethane (50 ml) stirred under argon at 0° C. was added neat DMF (34 μl, 0.439 mmol). The reaction mixture was stirred at 0° C. for 18 hr, then evaporated in vacuo and azeotroped with toluene (2×5 ml). The residue was dissolved in dichloromethane (50 ml), and to this were added DIPEA (0.908 ml, 5.20 mmol) and t-butyl carbazate (1259 mg, 9.53 mmol). The reaction mixture was stirred at room temp for 6 hr. The reaction mixture was partitioned between dichloromethane (˜50 ml) and saturated sodium bicarbonate solution (˜25 ml). The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined organic extracts washed with saturated sodium bicarbonate solution (˜50 ml), dried over sodium sulphate and evaporated in vacuo to give the crude product as a burgundy gum. This was purified via Biotage (5:1 DCM/MeOH; 40+M Biotage column; flow rate 20 ml/min) to afford impure product as a burgundy foam. This was further purified via Biotage (1:1 Hex/EtOAc; 40+M Biotage column) and dried overnight in a vacuum oven at 40° C. to afford the required product as a fine, pale yellow powder in 947.8 mg.

Provenance & Evidence