Dimethylformamide → N-Propyl-9-fluorene-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 9-fluorene carboxylic acid (20.0 g, 95 mmol) in 200 mL of CH2Cl2 was treated with oxalyl chloride (12.5 g, 105 mmol) and 0.2 mL of DMF. After 0.75 h, the mixture was concentrated under reduced pressure to give a white solid. The solid was diluted with 100 mL of THF cooled to -40° C., treated with propylamine (11.8 g, 200 mmol). The suspension was stirred for 3 h at room temperature and diluted with ethyl acetate and water. The organic fraction was dried over Na2SO4 and concentrated to a white solid. The solid purified by trituration with hot hexanes and recrystalization from hot methanol to give 17.5 g (87%) of title compound as white flakes. mp 197°-199° C.

Provenance & Evidence