Pyridine → Methyl 3-amino-2-bromo-4-methylbenzoate

A mixture of 16.5 g (100 mmol) of methyl 3-amino-4-methylbenzoate and 300 ml of CCl4 was treated with 18.6 g (105 mmol) of N-bromosuccinimide and stirred at ambient temperature for 4 hours. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure to afford an amber oil. To remove material resulting from bromination at the 6-position, the crude product was taken up in 100 ml of hexane and 60 ml of ether and treated with 3.96 g (50.0 mmol) of pyridine and 3.06 g (30.0 mmol) of acetic anhydride. After stirring for 3 hours at 25° C., the precipitate was removed by filtration. The filtrate was evaporated at reduced pressure to yield an amber oil. The crude product was purified by HPLC to afford 14.5 g (59%) of the desired product as an amber oil. IR and 1H NMR spectra were in agreement with the assigned structure.

1. filtrationThe reaction mixture was filtered
2. customthe filtrate was evaporated at reduced pressure
3. customto afford an amber oil
4. customTo remove material
5. customresulting from bromination at the 6-position
6. stirringAfter stirring for 3 hours at 25° C.
7. customthe precipitate was removed by filtration
8. customThe filtrate was evaporated at reduced pressure
9. customto yield an amber oil
10. customThe crude product was purified by HPLC

ORD record

ord-2f8989f2a33b4e9692f22ad39d9b4c24

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04755212