Water → HCID 19978637, compound

HRID 1089874Notes

Reaction equation

HRID 1089874 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.Cl[C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].O>[N+](C1C=CC=CC=1)([O-])=O.[Cu]=O>[C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1)([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 83742-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 19978637HCID 19978637, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 7416NitrobenzeneSolvent

Procedure

3-Indazolecarboxylic acid (4.10 g), 3.90 g of 2-chlorobenzoic acid, 3.90 g of potassium carbonate and 0.18 g of copper(II) oxide were stirred in 150 ml of nitrobenzene at 170° to 180° C. for 3 hours. After cooling, 100 ml of water was added to the reaction mixture, and the insoluble substance was removed by filtration. The resulting solution was washed with chloroform, and the aqueous layer was decolored with active charcoal and then filtered. The filtrate was made acidic with 50 ml of 1N hydrochloric acid and then extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was crystallized from methanol-chloroform-ether to obtain 2.13 g (30.2%) of 1-(2-carboxyphenyl)-3-indazolecarboxylic acid.

Workup

  1. temperatureAfter cooling
  2. customthe insoluble substance was removed by filtration
  3. washThe resulting solution was washed with chloroform
  4. filtrationfiltered
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol-chloroform-ether

Sources & evidence

ORD record
ord-a1a4537c64b346a59f7fba08729bc68b
Source dataset
uspto-grants-1992_01
Patent number
US05079358

Reaction notes

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