2,6-Dichloro-3-nitrotoluene → 2,4-Dichloro-m-toluidine

To a solution of 2,6-dichloro-3-nitrotoluene (50 g) in acetic acid (400 ml) and ethanol (200 ml) was added iron (67.8 g) and the mixture was refluxed for 1.5 hours under nitrogen atmosphere. The insoluble material was filtered off and the filtrate was concentrated. To the residue was added a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate three times. The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate three times and brine, dried over magnesium sulfate, and concentrated in vacuo to give 2,4-dichloro-3-methylaniline (41 g).

1. temperaturethe mixture was refluxed for 1.5 hours under nitrogen atmosphere
2. filtrationThe insoluble material was filtered off
3. concentrationthe filtrate was concentrated
4. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
5. extractionthe mixture was extracted with ethyl acetate three times
6. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate three times and brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo

ORD record

ord-93784639f3b24549957b68995566667a

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05750699