Formic Acid → 1-(3-Bromophenyl)ethanamine

Temperature

172.5 °C

A mixture of 3-bromoacetophenone (10.0 g, 50 mmol), formic acid (12.0 g, 250 mmol) and formamide (50 mL) was heated at 165-180° C. with stirring for 24 h. The reaction mixture was cooled to room temperature and extracted with toluene; the extract was concentrated in vacuo. The residue was mixed with 3N hydrochloric acid (20 mL) and heated at reflux for 48 h, cooled to room temperature, washed with ether and neutralized with 20% aqueous NaOH solution. The neutralized solution was extracted with ether; the extract was dried over solid KOH and concentrated in vacuo to provide the title compounds as a light brown oil (5.7 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.53 (s, 1 H), 7.37 (d, 1 H), 7.29 (d, 1 H), 7.21 (t, 1 H), 4.14 (br d, 3 H), 1.39 (d, 3 H). MS (ESI) m/z: Calculated: 199; Observed: 200 (M+H+).

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionextracted with toluene
3. concentrationthe extract was concentrated in vacuo
4. additionThe residue was mixed with 3N hydrochloric acid (20 mL)
5. temperatureheated
6. temperatureat reflux for 48 h
7. temperaturecooled to room temperature
8. washwashed with ether and neutralized with 20% aqueous NaOH solution
9. extractionThe neutralized solution was extracted with ether
10. dry with materialthe extract was dried over solid KOH
11. concentrationconcentrated in vacuo

ORD record

ord-8b0fe418024748ae96d007e20597a50e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604021B2