Dimethylformamide → HCID 69410881, compound

Participants

Reaction Steps

In N,N-dimethylformamide (“DMF”) (25 mL) was stirred 4-methoxy-1,3-benzenedicarboxylic acid (675 mg, 3.4 mmol) and potassium carbonate (4.3 g, 31 mmol). To this was added in parts, picolyl chloride hydrochloride (1.23 g, 7.5 mmol). The mixture was stirred at room temperature 24 hours. The mixture was filtered free of insoluble material and the DMF solution evaporated at reduced pressure to give a solid. This was partitioned between methylene chloride (100 mL) and saturated sodium bicarbonate solution (100 mL). The organic phase was separated and washed with water (100 mL) and then brine (100 mL). The organic phase was dried over magnesium sulfate and evaporated at reduced pressure to give 0.619 g (48%) of a tan solid. MS: M+1=379.1.

Provenance & Evidence