Methyl iodide → 3-Amino-2-methoxy-4-nitrobenzonitrile

HRID 501546Notes

Reaction equation

HRID 501546 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:14]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Product 1

HCID 597543533-Amino-2-methoxy-4-nitrobenzonitrileYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 11A (0.34 g, 1.86 mmol) and K2CO3 (0.283 g, 2.05 mmol) in DMF (3 mL) was added iodomethane (0.127 mL, 2.05 mmol). After the addition, the reaction mixture was stirred at rt for 16 h, then partitioned between H2O and CH2Cl2. The separated CH2Cl2 layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 5% to 40% EtOAc/hexane to yield the title compound (0.22 g) as a solid.

Workup

  1. additionAfter the addition
  2. custompartitioned between H2O and CH2Cl2
  3. washThe separated CH2Cl2 layer was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 5% to 40% EtOAc/hexane

Sources & evidence

ORD record
ord-b586bcadc939446697011a3c4515621d
Source dataset
uspto-grants-2010_08
Patent number
US07772267B2

Reaction notes

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