Methyl iodide → HCID 86671053, compound

HRID 1037358Notes

Reaction equation

HRID 1037358 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:15][O:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1497744720041-61-6

Product 1

HCID 86671053HCID 86671053, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-hydroxy-3-methoxy-4-nitro-benzaldehyde (10.4 g, 52.8 mmol, prepared as described in: J. Heterocyclic Chem., 1996, 33, 1171-78) in DMF (100 ml) was added potassium carbonate (11.04 g, 80 mmol), followed by methyl iodide (4 mL, 64 mmol) and the mixture stirred at 90° C. for 1 hour. The mixture was partitioned between ethyl acetate and water, separated, the organic phase was washed with brine, dried (Na2SO4), filtered, and the solvents were removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to give the title compound as a yellow oil (8.2 g, 74%). LCMS (Method B): RT=3.76 min, [M+H]+=212.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customseparated
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-09234e71811e46fd9d651d6dc94f0650
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…