Benzene, 1-chloro-2-methyl-4-nitro- → Benzenamine, 4-chloro-3-methyl-, hydrochloride (1:1)

Temperature

80 °C

Iron powder (150 g, 2.68 mol) and AcOH (600 mL) were charged into a 2 L round bottom flask equipped with a mechanical stirrer and thermometer. The mixture as warmed to 80° C. 4-Chloro-3-methylnitrobenzene (150 g, 0.87 mol) in AcOH (200 mL) was added slowly to the flask over 4 h, keeping the reaction temperature below 90° C. Upon consumption of the reactants, the mixture was filtered through a pad of Celite and the filter cake was washed with methanol (200 mL). The filtrate was concentrated and the residue was poured into 1.5 L of ice water (1:1) and the resulting precipitate was filtered. The crude product was dissolved in 300 mL 6N HCl in water/dioxane (1:1) and stirred at 100° C. for 3 h. It was then cooled to room temperature and the precipitate was filtered and dried to provide 130 g of 4-chloro-3-methyl-phenylamine hydrochloride as a colorless powder.

1. customequipped with a mechanical stirrer
2. customthe reaction temperature below 90° C
3. customUpon consumption of the reactants
4. filtrationthe mixture was filtered through a pad of Celite
5. washthe filter cake was washed with methanol (200 mL)
6. concentrationThe filtrate was concentrated
7. additionthe residue was poured into 1.5 L of ice water (1:1)
8. filtrationthe resulting precipitate was filtered
9. dissolutionThe crude product was dissolved in 300 mL 6N HCl in water/dioxane (1:1)
10. temperatureIt was then cooled to room temperature
11. filtrationthe precipitate was filtered
12. customdried

ORD record

ord-7f9a58cd1f6f4f80b7a229a64369c4be

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093247B2