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

HRID 852539Notes

Reaction equation

HRID 852539 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].[CH3:17]O>OS(O)(=O)=O>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 222530273-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoateYield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

3-Hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D36) (400 mg, 1.72 mmol, 1 equiv) was heated at reflux in a mixture of MeOH (20 ml) and concentrated H2SO4 (4 drops) for 7 h. The solution was then cooled to room temperature and concentrated in vacuo to give of 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D37) (300 mg, 74%) as a light brown solid.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a105ad78bba74e6c9c25fed913ee08d7
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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