Hydrochloric Acid → 3-Bromo-4-methoxyaniline

Temperature

80 °C

To a solution of N-(3-bromo-4-methoxyphenyl)acetamide III (5.0 g, 20.50 mmol) in EtOH (40.0 mL) was added concentrated HCl (20.0 mL) and heated the reaction mixture to 80° C. for 4-5 h. After the completion of the reaction (TLC monitoring), EtOH was distilled off and the residue was cooled to 0° C. followed by basification with aqueous NH3 till pH 12 and extraction with EtOAc (2×250 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product (3.56 g, 87%). 1H NMR (400 MHz, DMSO-d6): δ 3.67 (s, 3H), 4.88 (br s, 2H), 6.54 (dd, J=2.40 and 8.40 Hz, 1H) and 6.80 (m, 2H). MS: 202.17 (M+H)+.

1. distillationwas distilled off
2. temperaturethe residue was cooled to 0° C.
3. extractionfollowed by basification with aqueous NH3 till pH 12 and extraction with EtOAc (2×250 mL)
4. washThe combined organics was washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-8816b6abc7344dcea2ab3e2d5ccf25e7

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299065B2