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Hydrochloric Acid → 5-amino-1-(3-carboxyphenyl)-1H-pyrazole-4-carboxylic acid

HRID 399844
Notes
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Reaction equation

HRID 399844 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]=1[C:16]([O:18]CC)=[O:17].[OH-].[Na+].Cl>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][C:3]=1[C:16]([OH:18])=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 167772723-(5-amino-4-(ethoxycarbonyl)-1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 189453995-amino-1-(3-carboxyphenyl)-1H-pyrazole-4-carboxylic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

The mixture of 3-(5-amino-4-ethoxycarbonylpyrazol-1-yl)benzoic acid (5.9 g) and sodium hydroxide (2.1 g) in water (15 ml) was stirred for 2 hours at 80° C. To the reaction mixture was added water and the mixture was adjusted to pH 3.5 with 6N-hydrochloric acid. The isolated precipitate was collected by filtration washed with water and dried to give 3-(5-amino-4-carboxypyrazol-1-yl)benzoic acid (5.1 g).

Workup

  1. filtrationThe isolated precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-043b9028bc4541aebd08b5ad2391d552
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05824691

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes