Sulfamic Acid → 1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 1177923Notes

Reaction equation

HRID 1177923 reaction equation
S(=O)(=O)(O)N.[C:6]1([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl([O-])=[O:20].[Na+]>O.CC(C)=O>[C:6]1([N:12]2[CH:16]=[C:15]([C:17]([OH:20])=[O:18])[CH:14]=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 9520891-Phenyl-1H-pyrazole-4-carbaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 1210261-phenyl-1H-pyrazole-4-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Sulphamic acid (253 mg, 2.6 mmol) in water (0.5 mL) was added at 0° C. to a mixture of phenyl-1H-pyrazole-4-carbaldehyde (0.5 g, 2.34 mmol) in acetone (3 mL). After 5 minutes sodium chlorite (315 mg, 3.5 mmol) was added and the resulting mixture was stirred at 0° C. for 30 minutes. Water was added and the solid obtained was isolated by filtration to afford 140 mg (85% yield) of 1-phenyl-1H-pyrazole-4-carboxylic acid.

Workup

  1. customthe solid obtained
  2. customwas isolated by filtration

Sources & evidence

ORD record
ord-77a801d805b740d69df7c6baad44529e
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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