Potassium Hydroxide → HCID 90404007, compound

Temperature

2.5 °C

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.

1. customto produce an orange solution
2. additionthis solution was treated dropwise with commercial bleach solution (100 g, 5 wt. %, 67 mmol) over 30 min
3. customto produce a tan slurry
4. customThe cooling bath was removed
5. additiontreated with 600 mL water
6. filtrationthe solid product was collected by filtration
7. washwashed well with water
8. filtration150 mL water and filtered
9. customto remove a small amount of orange solids
10. washThe organic phase was washed with 75 mL saturated NaCl
11. dry with materialdried (Na2SO4)
12. customevaporated

ORD record

ord-c14fb33b208643f691fc1a2abec83faf

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006250B2