Toluene → (3-Amino-4-chlorophenyl)methanol

A 100 mL flask was charged with (4-chloro-3-nitrophenyl)methanol (commercially available from Acros; 1.0 g, 5.5 mmol), ammonium formate (1.4 g, 22 mmol), and iron powder (1.2 g, 22 mmol). Toluene (15 mL) and water (15 mL) were added to the flask and the mixture was heated to reflux for 4 hours, after which time, the mixture was filtered through a plug of Celite. The supernatant was washed with ethyl acetate (3×50 ml). The combined organic solution was washed with water (100 ml), saturated sodium chloride solution (100 ml), dried over anhydrous sodium sulfate and filtered. The organic solvent was removed on a rotary evaporator under reduced pressure to yield (3-amino-4-chlorophenyl)methanol (0.74 g, 85% yield). The material was used without further purification. 1H-NMR (400 MHz, CDCl3) δ 6.88 (d, 1H), 6.56 (d, 1H), 6.40 (s, 1H), 5.85 (bs, 2H), 5.39 (bs, 1H), 5.85 (bs, 1H), 4.79 (s, 2H): MS (EI): 158 (MH+).

1. temperaturethe mixture was heated
2. temperatureto reflux for 4 hours
3. filtrationafter which time, the mixture was filtered through a plug of Celite
4. washThe supernatant was washed with ethyl acetate (3×50 ml)
5. washThe combined organic solution was washed with water (100 ml), saturated sodium chloride solution (100 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customThe organic solvent was removed on a rotary evaporator under reduced pressure

ORD record

ord-dd190abce8154321b41a593680b10893

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088767B2