Methyl iodide → 2-Methoxy-5-nitrobenzonitrile

HRID 1597172Notes

Reaction equation

HRID 1597172 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12])#[N:2].[C:13]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[N+:9]([C:7]1[CH:6]=[CH:5][C:4]([O:12][CH3:13])=[C:3]([CH:8]=1)[C:1]#[N:2])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 111163772-Hydroxy-5-nitrobenzonitrile

Product 1

HCID 826772-Methoxy-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-cyano-4-nitrophenol (3.5 g, 21 mmol), K2CO3 (5.9 g, 42 mmol), and MeI (9.08 g, 64 mmol) in acetone (50 mL) was heated at reflux overnight. The mixture was cooled and concentrated, taken up in H2O, stirred, filtered the yellow solid, dried by air (3.0 g, 79%). 1H NMR (400 MHz, CDCl3): d 4.08 (s, 3H), 7.12 (d, J=9.2 Hz, 1H), 8.5 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. filtrationfiltered the yellow solid
  6. customdried by air (3.0 g, 79%)

Sources & evidence

ORD record
ord-c383916518ed4d8980d5fe45527822a9
Source dataset
uspto-grants-2001_09
Patent number
US06294531B1

Reaction notes

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