Methyl iodide → Methyl 2-hydroxy-3-nitrobenzoate

HRID 440669Notes

Reaction equation

HRID 440669 reaction equation
[Na].[N+:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]=1[OH:14])([O-:4])=[O:3].[CH3:15]I.[Cl-].[Li+]>CN(C)C=O>[N+:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:7]([C:8]([O:10][CH3:15])=[O:9])[C:6]=1[OH:14])([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 68073-Nitrosalicylic acidHCID 433294Lithium ChlorideHCID 5360545Sodium

Product 1

HCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flask are placed 5.0 g (0.024 mole) of the sodium salt of 3-nitrosalicylic acid, 3.58g (0.0252 mole) of methyl iodide, and 40 mL of N,N-dimethylformamide. This mixture is stirred at ambient temperature for approximately sixteen hours. At the conclusion of this period 200 mL of a 10% aqueous solution of lithium chloride is added to the reaction mixture. This mixture is extracted three times with ethyl acetate. The combined extracts are washed with 200 mL of the 10% aqueous solution of lithium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate is concentrated under reduced pressure, leaving a residue which is then passed through a column of silica gel, eluting with ethyl acetate. The product-containing fractions are combined, and the solvent is evaporated under reduced pressure leaving methyl 3-nitrosalicylate as a residue.

Workup

  1. customIn a flask are placed
  2. extractionThis mixture is extracted three times with ethyl acetate
  3. washThe combined extracts are washed with 200 mL of the 10% aqueous solution of lithium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customleaving a residue which
  8. washeluting with ethyl acetate
  9. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d8970a557e4a431db62059fac5fb0892
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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