HCID 178499179, compound → HCID 178524952, compound

HRID 1012093Notes

Reaction equation

HRID 1012093 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:20])[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:8][NH:7][N:6]=1)=[O:4]>[OH-].[Na+].CO>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[C:11]([NH:10][C:9]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][NH:7][CH:8]=1)=[O:20]

Participants

3

Reactant 1

HCID 178499179HCID 178499179, compound

Product 1

HCID 178524952HCID 178524952, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

A mixture of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester (1.21 g) in 2 M aqueous NaOH/MeOH (1:1, 50 ml) was stirred at ambient temperature for 14 hours. Volatile materials were removed in vacuo, water (100 ml) added and the mixture taken to pH 5 using 1M aqueous HCl. The resultant precipitate was collected by filtration and dried through azeotrope with toluene to afford 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid as a beige solid (790 mg). (LC/MS: Rt 2.53, [M+H]+ 299.95).

Workup

  1. customVolatile materials were removed in vacuo, water (100 ml)
  2. additionadded
  3. filtrationThe resultant precipitate was collected by filtration
  4. dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record
ord-bf6755f7d2cf42e9b1da8ced70438883
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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