Potassium Hydroxide → 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)benzoic acid

HRID 1988372Notes

Reaction equation

HRID 1988372 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)[CH:7]=[CH:6][C:5]=1[Cl:16].[OH-].[K+].CO.Cl>CO>[Cl:16][C:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:14]=[C:13]([CH3:15])[NH:12][N:11]=2)=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21893726Hydrochloride methanolHCID 588181962-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester

Product 1

HCID 184386602-chloro-5-(5-methyl-1H-pyrazol-3-yl)benzoic acidYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-5-(5-methyl-1H-pyrazol-3-yl)-benzoic acid methyl ester (4.5 g, 17.0 mmol) in methanol (20.0 mL) was treated with potassium hydroxide (4.52 g, 80.0 mmol). The mixture was stirred at room temperature for 16 h. The mixture was acidified to pH 4.0 with conc. HCl Methanol was removed from the mixture under vacuo. The residue was stirred at rt for 2 h and the solids collected by filtration, washed with water, 2:1 Hexanes/ether and dried to give the title compound (2.2 g)

Workup

  1. customwas removed from the mixture under vacuo
  2. stirringThe residue was stirred at rt for 2 h
  3. filtrationthe solids collected by filtration
  4. washwashed with water, 2:1 Hexanes/ether
  5. customdried

Sources & evidence

ORD record
ord-1560415e582441a5ae3329f8edaf3f05
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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