1,1-Dichloroethane → 3,5-Dinitroaniline

Participants

Reaction Steps

3,5-Dinitrobenzoic acid (7, Aldrich) (106.1 grams, 0.50 mole) was dissolved in 400 milliliters of 23 to 24% oleum. Dichloroethane (480 milliliters) was added to this solution. Sodium azide (37 grams, 0.57 mole) was added in portions with stirring while maintaining the temperature below 25° C. The mixture was heated under reflux for 4 hours and allowed to cool to room temperature. The dichloroethane was removed by decantation, and the remaining mixture was poured over 9 liters of ice mixed with water. The yellow solid which separated was filtered, washed with water, and air dried to afford 80.5 grams (87.9%) of 8 with a melting point of 158° to 162° C.; literature: melting point of 162° to 163° C. (Reference 10). IR (KBr) 3335 (d, NHz), 3035, 1615 (C=O), 1575, 1525, 1440, 1325, 1090, 1050, 990, 915, 880, 810 and 730 cm -1.

Provenance & Evidence