Ammonium Chloride → Methyl 3-(2-amino-5-bromophenylamino)-2-methylpropanoate

Temperature

60 °C

Iron powder (7 g, 0.12 mol) was added to a mixture of methyl 3-(5-bromo-2-nitrophenylamino)-2-methyl-propanoate (8 g, 25.2 mmol) in the mixed solvents of ammonium chloride aqueous (50 mL) and ethanol (100 mL). Once addition was completed, the mixture was heated to 60° C. for 2 hours. The mixture was filtered. The filtrate was concentrated, diluted with water (100 mL), extracted with ethyl acetate (150 mL×3). The organic layers were separated, combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to afford methyl 3-(2-amino-5-bromophenylamino)-2-methylpropanoate (6 g, 83%).

1. additionOnce addition
2. filtrationThe mixture was filtered
3. concentrationThe filtrate was concentrated
4. additiondiluted with water (100 mL)
5. extractionextracted with ethyl acetate (150 mL×3)
6. customThe organic layers were separated
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a residue
11. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

ORD record

ord-e4a2e9073d074f61a84f0fdfa5dacf7d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422292B2