Lithium hydroxide, monohydrate → 3-Cyclopropyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid

HRID 62452Notes

Reaction equation

HRID 62452 reaction equation
[CH:1]1([C:4]2[C:12]3[CH2:11][CH:10]([C:13]([O:15]C)=[O:14])[CH2:9][CH2:8][C:7]=3[NH:6][N:5]=2)[CH2:3][CH2:2]1.O[Li].O>CO.O>[CH:1]1([C:4]2[C:12]3[CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8][C:7]=3[NH:6][N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71223230HCID 71223230, compound

Product 1

HCID 712227663-Cyclopropyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution methyl 3-cyclopropyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylate (35.0 g) in MeOH (300 mL) was added a solution of LiOH.H2O (10.8 g, 0.26 mol) in H2O (200 mL) at 0° C. After stirring 18 h at rt the solvent was removed in vacuum. To the residue water (200 mL) was added and aqueous solution was acidified to pH=4-5 with 10% HCl. The precipitate was collected by filtration to give 3-cyclopropyl-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid (25.0 g, 80% yield for 2 steps).

Workup

  1. customwas removed in vacuum
  2. additionTo the residue water (200 mL) was added
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-57fc0213ea554b10af081c7d8cf37054
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

Loading…