Citric Acid → 2-{[2-(2-Oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic Acid

HRID 858948Notes

Reaction equation

HRID 858948 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])[CH:13]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[O:23]=[C:19]1[CH2:20][CH2:21][CH2:22][N:18]1[C:14]1[CH:13]=[C:12]([CH2:11][NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:24])=[O:2])[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58763660HCID 58763660, compound

Product 1

HCID 587636722-{[2-(2-Oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

700 mg (2.15 mmol) of 2-{[2-(2-oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic acid methyl ester is mixed in 15 ml of methanol with 2.7 ml of 1N sodium hydroxide solution and refluxed for 1 hour. After the methanol is distilled off in a vacuum, it is diluted with water and shaken once with ethyl acetate. The aqueous phase is mixed with 5 ml of 1 mol citric acid solution and stirred overnight. The solid precipitation is suctioned off and very quickly dried. 600 mg of 2-{[2-(2-oxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-benzoic acid, which is used as a crude product in the next stage, is obtained.

Workup

  1. temperaturerefluxed for 1 hour
  2. distillationAfter the methanol is distilled off in a vacuum, it
  3. additionis diluted with water
  4. stirringstirred overnight
  5. customThe solid precipitation
  6. customvery quickly dried
  7. customis obtained

Sources & evidence

ORD record
ord-01db8e51e2a8439a85f6edc76b32aceb
Source dataset
uspto-grants-2006_12
Patent number
US07148357B2

Reaction notes

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