Dimethylformamide → HCID 51051282, compound

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-phenyl-quinoline (40.0 g, 0.141 mol) was added to a 1000 mL three-neck round bottom flask (rbf). The flask was degassed and filled with N2. THF (400 mL) was added. The solid dissolved. The flask was kept in a cooling bath (at −62° C.). The off-white solid crashed out at low temperature. 1.4 M of sec-butyllithium in cyclohexane (125.7 mL, 0.176 mol) was added within 15 min, and the internal temperature was kept at around −50° C. After addition was complete, the reaction was stirred at −50° C. (internal temperature) for 5 min. DMF (13.6 mL, 0.176 mol) was added within 10 min and the internal temperature was always kept at around −50° C. and the cooling bath was kept at around at −62° C. After 35 min, the reaction was quenched by NH4Cl/water (200 mL), and EtOAc (200 mL) was added. The organic layer was washed with water (300 mL×2) and brine (150 mL), dried over MgSO4, filtered and concentrated in vacuo. After evaporating to almost dryness, EtOAc (200 mL) was added and heated in a 70° C. oil bath to dissolve the solid. Half of the aminodiphenylmethane (26.2 mL, 0.148 mol) was added and the reaction was stirred at 58° C. (internal temperature) for 5 min. The reaction was seeded and the solid came out of solution slowly. After 5 min, the remaining aminodiphenylmethane was added within 3 min. The oil bath temperature was kept at 70° C., the internal temperature increased to 67° C. After 10 min, the reaction mixture was cooled in an ice bath. The off-white solid was collected by vacuum filtration and dried in vacuo at 40-60° C. for 2 hours. The title compound was isolated as an off-white solid (37.42 g, 67% yield).

Provenance & Evidence