Lithium hydroxide, monohydrate → HCID 89740003, compound

HRID 2206470Notes

Reaction equation

HRID 2206470 reaction equation
O.[OH-].[Li+].[C:4]1([CH:10]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([O:23]C)=[O:22])=[N:13]2)[CH3:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.O>[C:4]1([CH:10]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([OH:23])=[O:22])=[N:13]2)[CH3:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 89740321HCID 89740321, compound

Product 1

HCID 89740003HCID 89740003, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a mixed solution of lithium hydroxide monohydrate (0.68 g, 16.8 mmol) in tetrahydrofuran (20 mL) and water (10 mL), methyl 1-(1-phenylethyl)-1H-indazole-3-carboxylate (2.3 g, 8.4 mmol) was added. The mixture was stirred at 45° C. for 12 hours. Then the organic solvent was removed under reduced pressure. To the residue, 1 N hydrochloride aqueous solution was added to adjust the pH to 3-4, and then the mixture was extracted with ethyl acetate (20 mL×3). The organic phase was combined, dried over anhydrous sodium sulfate, filtered and concentrated to afford 1-(1-phenylethyl)-1H-indazole-3-carboxylic acid (1.3 g, 60%) as a white solid, which was directly used in next step. LRMS (M+H+) m/z: calcd 266.29. found 266.

Workup

  1. customThen the organic solvent was removed under reduced pressure
  2. additionTo the residue, 1 N hydrochloride aqueous solution was added
  3. extractionthe mixture was extracted with ethyl acetate (20 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b75be0d6700d42e99e21ce28bbce9c94
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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