3-Aminophenol → 3-Azidophenol

An aqueous solution (15 mL) of NaNO2 (3.79 g, 54.98 mmol) was added dropwise to 3-aminophenol (5.0 g, 45 mmol) in 2 N HCl (100 mL) at 0-5° C. The solution was stirred for 30 minutes, followed by addition of an aqueous solution of sodium azide (4.5 g, 69 mmol, in 35 mL water). The mixture was stirred at room temperature for 24 h, and extracted with 300 mL of ethyl acetate. The combined organic layer was washed with water, and dried over MgSO4. Solvents were removed by rotary evaporation, and the residue was purified by column chromatography (EtOAc/hexanes, 1/4) to give the desired product as a dark red oil (4.52 g, 73% yield): 1H NMR (acetone-d6, 300 MHz, ppm): 8.69 (s, 1H, Ar—OH), 7.24 (t, 1H, J=8.1 Hz, Ar—H), 6.70-6.53 (m, 3H, Ar—H). 13C NMR (CDCl3, 75 MHz, ppm): 157.2, 141.6, 130.9, 112.4, 111.5, 106.5. FT-IR (cm−1): 3348, 2109.

1. stirringThe mixture was stirred at room temperature for 24 h
2. extractionextracted with 300 mL of ethyl acetate
3. washThe combined organic layer was washed with water
4. dry with materialdried over MgSO4
5. customSolvents were removed by rotary evaporation
6. customthe residue was purified by column chromatography (EtOAc/hexanes, 1/4)

ORD record

ord-52ac7e7cc7b149b2a99c80a26b7884cd

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895688B2