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

Temperature

90 °C

A mixture of methyl 5-bromo-2-methyl-3-nitrobenzoate (17 g, 62.0 mmol) in ethanol (85 mL) had NH4Cl solution (17 g in 85 mL water, 317.8 mmol) followed by Fe powder (27.8 g, 498.1 mmol) added. The resulting reaction mixture was stirred at 90° C. for 1 h. On completion, the reaction mixture was filtered and the filtrate was concentrated till dry. The resulting solid was dissolved in sat. sodium bicarbonate solution and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford solid methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 99.1%).

1. additionadded
2. customThe resulting reaction mixture
3. filtrationOn completion, the reaction mixture was filtered
4. concentrationthe filtrate was concentrated
5. customtill dry
6. dissolutionThe resulting solid was dissolved in sat. sodium bicarbonate solution
7. extractionextracted with ethyl acetate
8. dry with materialThe combined organic layers were dried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-440243dcfd864e3bbf87ad19c2e266d9

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962620B2