Methanol → 2-Hydroxy-6-nitrobenzonitrile

HRID 471584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471584
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+]([O-])=O)[C:5]=1[C:6]#[N:7])([O-:3])=[O:2].Cl.N1C=CC=CC=1.C[OH:23]>>[OH:23][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[C:6]#[N:7]

Komponenten

4

Edukt 3

HCID 887Methanol2×HCID 520718DinitrobenzonitrileHCID 10176127Pyridinium chloride

Produkt 1

HCID 125032052-Hydroxy-6-nitrobenzonitrileAusbeute 87 %

Versuchsvorschrift

To a solution of 2,6-dinitrobenzonitrile (10.0 g, 52.3 mmol) in MeOH (215 mL), was added a solution of Na (1.32 g, 57.5 mmol) in MeOH (23.3 mL). The reaction was refluxed under N2 for 2.5 hours, cooled to rt and the precipitate was collected by filtration. The resulting residue was combined with pyridine hydrochloride (15.1 g, 130 mmol), and the solids were melted at 200° C. for 18 hours. Upon completion, the reaction was cooled to rt, washed with brine (1×300 mL) and extracted with EtOAc (2×500 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated to provide 2-hydroxy-6-nitrobenzonitrile (6.70 g, 87%). 1H NMR (400 MHz, MeOD) δ 7.35 (dd, J=8.3, 0.8 Hz, 1H), 7.67 (t, J=8.2 Hz, 1H), 7.77 (dd, J=8.2, 1.1 Hz, 1H).

Aufarbeitung

  1. temperatureThe reaction was refluxed under N2 for 2.5 hours
  2. filtrationthe precipitate was collected by filtration
  3. customfor 18 hours
  4. temperatureUpon completion, the reaction was cooled to rt
  5. washwashed with brine (1×300 mL)
  6. extractionextracted with EtOAc (2×500 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-23ff5519962d464aa47227501d406cfd
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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