Methanol → 2-Methoxy-6-nitrobenzonitrile

HRID 711732Notes

Reaction equation

HRID 711732 reaction equation
[Na].[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([N+]([O-])=O)[C:6]=1[C:7]#[N:8])([O-:4])=[O:3].[CH3:16][OH:17]>>[CH3:16][O:17][C:9]1[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=1[C:7]#[N:8]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 520718DinitrobenzonitrileHCID 5360545Sodium

Product 1

HCID 380482-Methoxy-6-nitrobenzonitrileYield 94%

Procedure

A solution of sodium methoxide, obtained by adding sodium (1.68 g, 73.1 mmol) to anhydrous MeOH (73 mL), was added to 2,6-dinitrobenzonitrile (13.20 g, 68.4 mmol) in dry MeOH (284 mL) under nitrogen at room temperature over 10 min. The reaction was refluxed for 1 hour, and then MeOH was removed under vacuum. Dichloromethane (400 mL) was added, and the insoluble solids were filtered out. The organic layer was washed with brine (100 mL), dried with MgSO4, and removed under vacuum to give 11.45 g (94%) of 2-methoxy-6-nitrobenzonitrile, which was used without further purification. 1H-NMR (400 MHz, DMSO-d6) δ 7.87-7.94 (m, 2H), 7.68-7.75 (m, 1H), 4.01 (s, 3H).

Workup

  1. temperatureThe reaction was refluxed for 1 hour
  2. customMeOH was removed under vacuum
  3. additionDichloromethane (400 mL) was added
  4. filtrationthe insoluble solids were filtered out
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried with MgSO4
  7. customremoved under vacuum

Sources & evidence

ORD record
ord-c8c22ff057b24fc3815a44bed894bde9
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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