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

HRID 2382970Notes

Reaction equation

HRID 2382970 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=1)=[O:4].[OH-].[Na+].Cl>O.CO>[C:14]([C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[N:8][N:9]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:10]=2[CH:11]=1)#[N:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 581388956-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester

Product 1

HCID 581389176-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester (0.30 g, 1.1 mmol) in water (10 mL) and methanol (10 mL) was added a 2 N aqueous sodium hydroxide (10 mL, 20 mmol). The mixture was warmed at reflux for 1 hour, cooled to room temperature, and acidified with 1 N aqueous HCl (pH=3-4). The white solid was collected by filtration, washed with MeOH (10 mL) and dried to afford 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 1 hour
  3. filtrationThe white solid was collected by filtration
  4. washwashed with MeOH (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-d490f3c0a93049ea80756c5013bb94c2
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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