1,2-Dimethyl-3-nitrobenzene → HCID 18629320, compound

The mixture of 90.60 g of 2,3-dimethylnitrobenzene (3-10) and 1.20 g of iron powder was heated at 75° C., to which 115.00 g of bromine was dropped with stirring, and then the resulting mixture was stirred at the same temperature for 4 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate, and the resulting organic layer was washed with sodium thiosulfate solution and saturated salt water in order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and 400 ml of methanol and 400 ml of concentrated hydrochloric acid were added to the resulting residue, to which 100 g of iron powder was added in a divided form, and thereafter, the resulting mixture was stirred at 70° C. for 30 minutes. The reaction solution was poured into ice water, and the resulting mixture was alkaline with sodium bicarbonate, and thereafter, extracted with ethyl acetate and the resulting organic layer was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane:ethylacetate=9:1) to obtain 48.82 g of 5-bromo-2,3-dimethylaniline (3-11).

1. additionwas dropped
2. stirringthe resulting mixture was stirred at the same temperature for 4 hours
3. extractionextracted with ethyl acetate
4. washthe resulting organic layer was washed with sodium thiosulfate solution and saturated salt water in order
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure and 400 ml of methanol and 400 ml of concentrated hydrochloric acid
7. additionwere added to the resulting residue, to which 100 g of iron powder
8. additionwas added in a divided form
9. stirringthe resulting mixture was stirred at 70° C. for 30 minutes
10. additionThe reaction solution was poured into ice water
11. extractionextracted with ethyl acetate
12. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
13. customThe solvent was removed under reduced pressure
14. customthe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethylacetate=9:1)

ORD record

ord-68f61533f66c4f4086bce985c292728d

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525066B2