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

HRID 852540Notes

Reaction equation

HRID 852540 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6](N)[CH:5]=1.[N-]=[N+]=[N-].[Na+].[OH2:22]>Cl.CO.CCOCC>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([OH:22])[CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 674420033-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

Product 1

HCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoateYield 67%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

3-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D4a) (1.50 g, 6.4 mmol, 1 equiv) was dissolved in a mixture of 2N aqueous HCl solution (25 ml) and MeOH (50 ml) at 0° C. and treated portionwise with NaN3 (950 mg, 13.8 mmol, 2.2 equiv) over 20 min. H2O (50 ml) was added and the resulting mixture was heated at 90° C. for 45 min then cooled to room temperature and diluted with Et2O (300 ml). The two layers were separated and the organic phase was dried over MgSO4 and concentrated in vacuo to give 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D37) (1.0 g, 67%) as a tan solid.

Workup

  1. temperaturethen cooled to room temperature
  2. customThe two layers were separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db0c0a5ea7134b99a8b82817089f9646
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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