Ammonium Chloride → Methyl 3-Amino-5-bromo-2-methylbenzoate

Temperature

80 °C

To stirred solution of methyl 5-bromo-2-methyl-3-nitrobenzoate (290 g, 1060 mmol) in ethanol (1.5 L) was added aqueous ammonium chloride (283 g, 5290 mmol dissolved in 1.5 L water). The resulting mixture was stirred and heated at 80° C. followed by addition of iron powder (472 g, 8450 mmol) in portions at 80° C. The resulting reaction mixture was heated at 80° C. for 12 h. After completion, the reaction mixture was hot filtered over celite and the celite bed was washed with methanol (5 L) followed by washing with 30% MeOH in DCM (5 L). The combined filtrate was concentrated in-vacuo, the residue obtained was diluted with aqueous bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to afford the title compound as brown solid (220 g, 89% yield).

1. customThe resulting reaction mixture
2. temperaturewas heated at 80° C. for 12 h
3. filtrationAfter completion, the reaction mixture was hot filtered over celite
4. washthe celite bed was washed with methanol (5 L)
5. washby washing with 30% MeOH in DCM (5 L)
6. concentrationThe combined filtrate was concentrated in-vacuo
7. customthe residue obtained
8. extractionextracted with ethyl acetate
9. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-cb8972a58fad4549baf195b0ddea931a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376422B2