1,2-Dimethyl-3,5-dinitrobenzene → 2,3-Dimethyl-5-nitroaniline

1,2-Dimethyl-3,5-dinitrobenzene (2.5 g, prepared as described in the above scheme) was dissolved in glacial acetic acid (25 mL, from Mallinckrodt) under N2 and heated to reflux. The heat source was removed and iron (2.13 g) was added all at once. After the initial vigorous reaction, the mixture was heated at reflux for 10 min and then cooled to room temperature. The reaction mixture was filtered through a celite pad and washed with ethyl acetate. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and refiltered through a celite pad and then washed with saturated sodium bicarbonate solution and half-saturated sodium chloride solution. After drying over magnesium sulfate and evaporation of the solvent, 2,3-dimethyl-5-nitro-phenylamine (1.41 g) was obtained.

1. temperatureheated to reflux
2. customThe heat source was removed
3. additioniron (2.13 g) was added all at once
4. customAfter the initial vigorous reaction
5. temperaturethe mixture was heated
6. temperatureat reflux for 10 min
7. filtrationThe reaction mixture was filtered through a celite pad
8. washwashed with ethyl acetate
9. customThe filtrate was evaporated under reduced pressure
10. dissolutionThe residue was dissolved in ethyl acetate
11. washwashed with saturated sodium bicarbonate solution and half-saturated sodium chloride solution
12. dry with materialAfter drying over magnesium sulfate and evaporation of the solvent

ORD record

ord-caf3009854ab4ae1a6d1c9f02df64031

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057349