Hydrochloric Acid → 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

HRID 2172956Notes

Reaction equation

HRID 2172956 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].[OH-].[Na+].Cl>O.CO>[F:20][C:17]1[CH:16]=[CH:15][C:14]([N:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=3[CH:7]=[N:8]2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 581388911-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester

Product 1

HCID 581387741-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester (2.0 g, 7.4 mmol) in water (20 mL) and methanol (20 mL) is added a solution of 2N sodium hydroxide (10 mL). The solution is warmed at reflux for 1 hour. The solution is cooled to room temperature and acidified to pH 3-4 with 1N aqueous HCl. The mixture is filtered, and the resulting solid is washed with MeOH (30 mL) and dried to afford 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid.

Workup

  1. temperatureThe solution is warmed
  2. temperatureat reflux for 1 hour
  3. filtrationThe mixture is filtered
  4. washthe resulting solid is washed with MeOH (30 mL)
  5. customdried

Sources & evidence

ORD record
ord-6592ac20f3cf4c85a37587f1531795c8
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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