Methyl iodide → Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 1612452Notes

Reaction equation

HRID 1612452 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:17](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 222530273-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid (D6) (1.20 g, 5.43 mmol) and cesium carbonate (1.77 g, 5.43 mmol) in DMF (10 ml) was sonicated for 15 minutes. Iodomethane (0.372 ml, 5.97 mmol) was added and the mixture was stirred at room temperature. After 1 hr more iodomethane (0.05 ml) was added and stirring was continued for a further 30 minutes. The solvent was evaporated, ethyl acetate and 2N HCl were added and the product was extracted into ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and concentrated. Purification by trituration with ethyl acetate and/or chromatography on silica gel (elution with ethyl acetate) gave the title compound (D41). (1.042 g).

Workup

  1. customwas sonicated for 15 minutes
  2. stirringstirring
  3. customThe solvent was evaporated
  4. additionethyl acetate and 2N HCl were added
  5. extractionthe product was extracted into ethyl acetate
  6. washThe extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification by trituration with ethyl acetate and/or chromatography on silica gel (elution with ethyl acetate)

Sources & evidence

ORD record
ord-67afb720e1bb4fe78bfcb0eec5b25c71
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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