Methanol → Methyl 4-(2-oxopyrrolidin-1-yl)benzoate

HRID 1635551Notes

Reaction equation

HRID 1635551 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[CH:6][CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:21][O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7731304-(2-Oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 757827Methyl 4-(2-oxopyrrolidin-1-yl)benzoateYield 94%

Procedure

A mixture of 1-(4-carboxyphenyl)pyrrolidin-2-one (3.0 g, 14.6 mmol) from example 1 and sulfuric acid (0.2 mL) in 100 mL of methanol was stirred at reflux for 18 h. The solvent was removed under vacuum. The crude material was dissolved in 100 mL of ethyl acetate and the solution was washed with a saturated sodium bicarbonate solution (3×15 mL), dried and evaporated to give 3.0 g (94%) of 1-(4-methoxycarbonylphenyl)pyrrolidin-2-one as a white solid, mp 118-120° C. (chloroform/ether).

Workup

  1. temperatureat reflux for 18 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe crude material was dissolved in 100 mL of ethyl acetate
  4. washthe solution was washed with a saturated sodium bicarbonate solution (3×15 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-667e29fec42d4dad823fe776988d5dde
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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