Hydrochloric Acid → 3-(5-Aminopyrazol-1-yl)benzoic acid

HRID 399845Notes

Reaction equation

HRID 399845 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])[N:5]=[CH:4][C:3]=1C(O)=O.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>COCCOCCOC.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=[O:11])[N:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 189453995-amino-1-(3-carboxyphenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 189452753-(5-Aminopyrazol-1-yl)benzoic acidYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

The mixture of 3-(5-amino-4-carboxypyrazol-1-yl)benzoic acid (19.4 g) in diglyme (200 ml) was heated under reflux for 6 hours. To the mixture was added a mixture of ethyl acetate and water, and adjusted to pH 9 with 20% aqueous potassium carbonate solution. The separated aqueous layer was adjusted to pH 3.5 with 6N-hydrochloric acid and the mixture was extracted with a solution of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give 3-(5-aminopyrazol-1-yl)benzoic acid (7.59 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. additionTo the mixture was added
  4. extractionthe mixture was extracted with a solution of ethyl acetate and tetrahydrofuran
  5. washThe extract layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f9c204d4be84050a73219bb4f0f3ae9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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