Hydrochloric Acid → 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

HRID 2382960Notes

Reaction equation

HRID 2382960 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4].[OH-].[Na+].Cl>O.CO>[Br:14][C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[N:8][N:9]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[C:10]=2[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 581387736-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester

Product 1

HCID 581389136-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester (1.7 g, 4.8 mmol) in water (15 mL) and methanol (15 mL) was added a solution of 2 N aqueous sodium hydroxide (10 mL, 20 mmol). The solution was warmed at reflux for 1 hour. The reaction mixture was cooled to room temperature and acidified with 1 N aqueous HCl (pH=3-4) to afford a precipitate which was collected by filtration, washed with MeOH and air dried to afford 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid.

Workup

  1. temperatureThe solution was warmed
  2. temperatureat reflux for 1 hour
  3. customto afford a precipitate which
  4. filtrationwas collected by filtration
  5. washwashed with MeOH and air
  6. customdried

Sources & evidence

ORD record
ord-33bbe6e4d42b4e2da269e359823199ab
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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