Lithium Hydroxide → 1-Methyl-1H-indazole-5-carboxylic acid

HRID 1880386Notes

Reaction equation

HRID 1880386 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13]C)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[Li+].[OH-].OS([O-])(=O)=O.[K+]>CO.O.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 37818676Methyl 1-methyl-1H-indazole-5-carboxylate

Product 1

HCID 391037571-Methyl-1H-indazole-5-carboxylic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 1-methyl-1H-indazole-5-carboxylate (107 mg, 0.56 mmol) in methanol/water (V:V 1:1, 4 mL) was added LiOH (48 mg). The solution was heated at 40° C. for 3 hours before cooling to room temperature. The mixture was diluted with water and acidified to pH 3.5-4 with KHSO4. Solids precipitated and were isolated by filtration and dried under vacuum to afford the title compound as a yellow solid (70 mg, 71%).

Workup

  1. temperaturebefore cooling to room temperature
  2. customSolids precipitated
  3. customwere isolated by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ff5c23545483430f88175547e541a4d5
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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