HCID 178499177, compound → 4-(4-Methylbenzamido)-1H-pyrazole-5-carboxylic acid

HRID 1012112Notes

Reaction equation

HRID 1012112 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:8][NH:7][N:6]=1)=[O:4]>[OH-].[Na+].CO>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][NH:7][CH:8]=2)=[O:19])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 178499177HCID 178499177, compound

Product 1

HCID 1784258454-(4-Methylbenzamido)-1H-pyrazole-5-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

A mixture of 4-(4-methyl-benzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester (486 mg) in 2 M aqueous NaOH/MeOH (1:1, 50 ml) was stirred at ambient temperature for 14 h. Volatile materials were removed in vacuo, water (100 ml) added and the mixture taken to pH 5 using 2M aqueous HCl. The resultant precipitate was collected by filtration and dried through azeotrope with toluene to afford 4-(4-methyl-benzoylamino)-1H-pyrazole-3-carboxylic acid as a gray solid (345 mg). (LC/MS: Rt 2.35, [M+H]+ 246.09).

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-901c7a0f6d5a4467ad5b1f2978ede50c
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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