Acetic Acid → 3-Amino-4-chlorophenol

Temperature

100 °C

A 100-mL round bottomed flask equipped with a magnetic stir bar was charged with 4-chloro-3-nitrophenol (6.0 g, 34.6 mmol) and acetic acid (60 mL). Iron powder (325 mesh) (19.31 g, 346 mmol) was added, and the mixture was heated at 100° C. for 30 min. The mixture was cooled to room temperature and diluted with water (40 mL). The mixture was then filtered through a pad of Celite and rinsed with water. The filtrate was then extracted with ethyl acetate, and the combined extracts were concentrated under reduced pressure. Heptane (ca. 100 mL) was added to the filtrate and then removed under reduced pressure in order to remove residual acetic acid and water. This was repeated. The residue was dissolved in acetonitrile and concentrated under reduced pressure. The resulting solid was suspended in heptane and concentrated under reduced pressure to afford 3-amino-4-chlorophenol (4.38 g, 88%) as a pale purple/amber solid. MS (ESI, pos. ion) m/z 144 [M+1].

1. customA 100-mL round bottomed flask equipped with a magnetic stir bar
2. temperatureThe mixture was cooled to room temperature
3. filtrationThe mixture was then filtered through a pad of Celite
4. washrinsed with water
5. extractionThe filtrate was then extracted with ethyl acetate
6. concentrationthe combined extracts were concentrated under reduced pressure
7. additionHeptane (ca. 100 mL) was added to the filtrate
8. customremoved under reduced pressure in order
9. customto remove residual acetic acid and water
10. dissolutionThe residue was dissolved in acetonitrile
11. concentrationconcentrated under reduced pressure
12. concentrationconcentrated under reduced pressure

ORD record

ord-28d5df9a63a648158c93abeee91da03b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388161B2