Dimethylformamide → N-propylphenyl-3-formylcarbazole

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Reaction Steps

To a 500 ml, three neck round bottom flask equipped with mechanical stirrer, thermometer, and addition funnel were added N-propylphenylcarbazole (56g, 0.2 mol) (prepared as described in the procedure used to prepare Compound (6)) and DMF (300 ml). The flask was placed in an ice/salt bath. When the temperature inside the flask reached 0° C., POCl3 (21 ml, 0.22 mol) was added slowly by the addition funnel. The inside temperature was not allowed to rise above 5° C. during the addition of the POCl3. When the addition of POCl3 was completed, the flask was placed on a steam bath for 2 hr. The flask was cooled to room temperature, then added slowly to a large excess of water (2 liters in a 4.5 liter beaker). The solution was stirred at room temperature for 3 hr, the solid was filtered off, washed repeatedly with water, and followed by washing with ethanol (20 ml). The product was recrystallized once from THF/water and dried at 60° C. in a vacuum oven for 6 hr. to produce 50 g (79% yield) of N-propylphenyl-3-formylcarbazole. 1H-N MR and IR spectra confirmed the structure of the product.

Provenance & Evidence