Citric Acid → 2-Chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-benzoic acid

HRID 1988374Notes

Reaction equation

HRID 1988374 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)[CH:8]=[CH:7][C:6]=1[Cl:19])C.[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Cl:19][C:6]1[CH:7]=[CH:8][C:9]([C:11]2[CH:15]=[C:14]([CH:16]3[CH2:17][CH2:18]3)[NH:13][N:12]=2)=[CH:10][C:5]=1[C:4]([OH:20])=[O:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 588181832-chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-benzoic acid ethyl ester

Product 1

HCID 184386582-Chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-benzoic acidYield 134.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-5-(5-cyclopropyl-1H-pyrazol-3-yl)-benzoic acid ethyl ester (0.05 g, 0.17 mmol) in methanol (4 mL) was added KOH (0.12 g). The mixture was shaken at room temperature for 16 h. The mixture was acidified with 10% aqueous citric acid and extracted with ethyl acetate. The combined organic layers were washed with water and brine, and concentrated in vacuo to afford the title compound (0.06 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11a6d3cd8ce34dda80cbdef098516508
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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