Nitric Acid → 4-Bromo-2-methyl-6-nitroaniline

Beteiligte Stoffe

Reaktionsschritte

[step 1] To a mixture of 4-bromo-2-methylaniline (9.00 g, 48.3 mmol) and acetic anhydride (54 mL) was added dropwise under ice-cooling fuming nitric acid (8.10 mL, 194 mmol) over 20 min. Under ice-cooling, the mixture was stirred for 1 hr and water and ethyl acetate were added to the mixture, and the mixture was extracted. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate-hexane (1/1, 24 mL) was added to the residue, and the precipitated solid was collected by filtration. The obtained solid was suspended in ethanol (40 mL), concentrated hydrochloric acid (25 mL) was added, and the mixture was stirred under reflux for 4 hr. To the mixture were added ethanol (10 mL) and water (7 mL), and the mixture was stirred at 90° C. for 30 min. The reaction solution was allowed to cool to room temperature, and the precipitated solid was collected by filtration to give 4-bromo-6-methyl-2-nitroaniline (3.87 g, 35%).

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