Hydrochloric Acid → 3-Bromo-4-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence