Hydrochloric Acid → 6-Bromo-1-methyl-1H-indazole-4-carboxylic acid

HRID 520552Notes

Reaction equation

HRID 520552 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([C:14]([O:16]C)=[O:15])[C:7]2[CH:8]=[N:9][N:10]([CH3:13])[C:11]=2[CH:12]=1.Cl>O1CCCC1.O>[Br:3][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[CH:8]=[N:9][N:10]([CH3:13])[C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66691568methyl 6-bromo-1-methyl-1H-indazole-4-carboxylate

Product 1

HCID 666914996-Bromo-1-methyl-1H-indazole-4-carboxylic acidYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (156 mg, 6.51 mmol) was added to a stirred suspension of methyl 6-bromo-1-methyl-1H-indazole-4-carboxylate (730 mg, 2.71 mmol) in tetrahydrofuran (THF) (25 ml) and water (5 ml) and the reaction mixture was stirred at room temperature for 1 h. During this time the cream suspension turned to a pale brown solution. The reaction mixture was poured onto 2N HCl (100 ml) with stirring. The precipitate formed was filtered off under vacuum and dried at 50° C. in a vacuum oven for 18 h to give the title compound as a white solid (480 mg).

Workup

  1. stirringwith stirring
  2. customThe precipitate formed
  3. filtrationwas filtered off under vacuum
  4. customdried at 50° C. in a vacuum oven for 18 h

Sources & evidence

ORD record
ord-d580f029781a438c8ce05dd4d7636510
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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