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

HRID 471590

Reaction equation

HRID 471590 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

3

Reactant 2

HCID 2886654-Methoxy-2-nitrobenzonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 534181214-Hydroxy-2-nitrobenzonitrileYield 26.5%

Conditions

Temperature
200 °C

Procedure

A mixture of 4-methoxy-2-nitrobenzonitrile (820 mg, 4.6 mmol) and pyridine hydrochloride (755 mg, 4.6 mmol) was heated at 200° C. under N2 for 18 hours. Upon completion, the reaction was cooled to room temperature, washed with brine and extracted with EtOAc (2×100 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (1:1 Hexane:EtOAc) to provide 4-hydroxy-2-nitrobenzonitrile (200 mg, 26%). 1H NMR (400 MHz, MeOD) δ 7.24 (dd, J=8.6, 2.4 Hz, 1H), 7.70 (d, J=2.4 Hz, 1H), 7.83 (d, J=8.6 Hz, 1H).

Workup

  1. temperatureUpon completion, the reaction was cooled to room temperature
  2. washwashed with brine
  3. extractionextracted with EtOAc (2×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (1:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-2e57716406dd41798765c53b1afdb0e0
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

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