Lithium Hydroxide → 6-methyl-1H-indazole-5-carboxylic acid

HRID 1269870Notes

Reaction equation

HRID 1269870 reaction equation
[OH-].[Na+].C([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:16]([O:18]C)=[O:17])=[C:12]([CH3:15])[CH:13]=2)[CH:8]=[N:7]1)(=O)C.[OH-].[Li+]>O1CCCC1.O>[CH3:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[N:7][NH:6]2)=[CH:10][C:11]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 22933897methyl 1-acetyl-6-methyl-1H-indazole-5-carboxylate

Product 1

HCID 229340406-methyl-1H-indazole-5-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2N-aqueous sodium hydroxide solution (0.63 ml, 1.3 mmol) was added to a solution of methyl 1-acetyl-6-methyl-1H-indazole-5-carboxylate (0.0731 g, 0.315 mmol) in tetrahydrofuran (1 ml), and the resulting mixture was stirred for 3 hours with heating under reflux. Then, a 2N-aqueous lithium hydroxide solution (0.63 ml, 1.3 mmol) was added thereto and stirred for another 3 hours. The resulting solution was diluted with water and washed with diethyl ether, and the aqueous layer was adjusted to pH 1 to 2 with 1N-hydrochloric acid to precipitate a solid. The solid precipitated was collected by filtration and the precipitate on a filter was washed with water and dried under reduced pressure to obtain 6-methyl-1H-indazole-5-carboxylic acid (0.0514 g, 93%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. stirringstirred for another 3 hours
  4. washwashed with diethyl ether
  5. customto precipitate a solid
  6. customThe solid precipitated
  7. filtrationwas collected by filtration
  8. washthe precipitate on a filter was washed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-38e9d241bf304d9a9bf6d2fa1d89fdac
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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