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Hydrochloric Acid → 2-(2,4-Dimethylbenzyl)-3-(4-fluorophenyl)-2H-indazole-7-carboxylic acid

HRID 735440
Notes
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Reaction equation

HRID 735440 reaction equation
[CH3:1][C:2]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:12]2[C:7]([C:8]([C:21]([O:23]C)=[O:22])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:12]2[C:7]([C:8]([C:21]([OH:23])=[O:22])=[CH:9][CH:10]=[CH:11]2)=[N:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11696743methyl 2-(2,4-dimethylbenzyl)-3-(4-fluorophenyl)-2H-indazole-7-carboxylate

Product 1

HCID 670212802-(2,4-Dimethylbenzyl)-3-(4-fluorophenyl)-2H-indazole-7-carboxylic acidYield 0.5%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Conditions

Temperature
50 °C

Procedure

A solution of methyl 2-(2,4-dimethylbenzyl)-3-(4-fluorophenyl)-2H-indazole-7-carboxylate (0.195 g, 0.5 mmol) in 5 mL methanol was treated with 1 mL of 1N NaOH and stirred at 50° C. for 1 hour. The solution was neutralized with dilute HCl and partitioned with ethyl acetate and H2O. The organic phase was dried (Na2SO4) and concentrated in vacuo to give 0.95 mg of the title compound as a yellow solid.

Workup

  1. custompartitioned with ethyl acetate and H2O
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78731feab545482c901a9ad2c7579301
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592363B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes