4-Nitroaniline → HCID 136025189, compound

Participants

Reaction Conditions

Reaction Steps

In a small beaker was suspended 3.0 g (21.7 mmol) of p-nitro aniline in 24 ml 5N HCl and 6 ml of distilled water. The suspension was cooled to 0° C. in an ice bath and 1.6 g of NaNO2 dissolved in 5 ml of water was slowly added via a pipette over 15 minutes while the temperature of the suspension was kept under 4° C. When all the sodium nitrite had been added, the suspension was stirred for an additional 1 hour. In a separate beaker were combined 12 g sodium acetate, 24 ml of acetic acid and 4.5 g of the 3-(N,N-diallylamino)phenol, and the beaker was cooled to ca. 0° C. The contents of the first beaker were added to the second beaker slowly with stirring. After 2 hours, the mixture was poured into 100 ml of ice water and saturated aqueous sodium bicarbonate solution was added until the foaming stopped. The red solid was filtered, washed with excess distilled water and dried in a vacuum desiccator overnight to yield 6.4 g of N,N-diallyl-4-(4'-nitrophenylazo)-3-hydroxyaniline.

Provenance & Evidence