Potassium Hydroxide → HCID 90404007, compound

Participants

Reaction Conditions

Reaction Steps

4-bromo-3-methyl-2-nitroaniline (8.2 g, 36 mmol) was stirred in 150 mL ethanol, treated with potassium hydroxide solution (4.4 g, 45 wt. %, 36 mmol) to produce an orange solution. After cooling to 0-5° C., this solution was treated dropwise with commercial bleach solution (100 g, 5 wt. %, 67 mmol) over 30 min to produce a tan slurry. The cooling bath was removed and the mixture was stirred for 30 min more, treated with 600 mL water and the solid product was collected by filtration and washed well with water. The wet solid was taken up in 350 mL ethyl acetate and 150 mL water and filtered to remove a small amount of orange solids. The organic phase was washed with 75 mL saturated NaCl, dried (Na2SO4) and evaporated to give the title compound which was carried on to the deoxygenation step without further purification (7 g, 85%): EIMS m/z 228.

Provenance & Evidence