2-Methoxy-4-nitrobenzonitrile → 2-Hydroxy-4-nitrobenzonitrile

Temperature

160 °C

To a solution of 2-methoxy-4-nitrobenzonitrile (5.0 g, 28.1 mmol) in N,N-dimethylformamide (28 mL) was added lithium chloride (2.38 g, 56.2 mmol), and the mixture was stirred at 160° C. for 16 hr. The reaction solution was cooled to room temperature, diluted with ethyl acetate (300 mL), washed with 1% aqueous citric acid solution (150 mL), water (150 mL) and saturated brine (150 mL×2), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70), and the obtained solution was concentrated under reduced pressure. The residue was triturated with ethyl acetate to give the title compound (3.98 g, 86%) as a yellow-brown solid.

1. temperatureThe reaction solution was cooled to room temperature
2. washwashed with 1% aqueous citric acid solution (150 mL), water (150 mL) and saturated brine (150 mL×2)
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationThe insoluble material was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70)
7. concentrationthe obtained solution was concentrated under reduced pressure
8. customThe residue was triturated with ethyl acetate

ORD record

ord-960b7003a5fa400eb6c1cf229bfd629a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2