Water → 5-(Aminomethyl)-1H-indazole

HRID 1269734Notes

Reaction equation

HRID 1269734 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Li+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 111263841H-Indazole-5-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 120962235-(Aminomethyl)-1H-indazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1H-indazole-5-carbonitrile (100 mg, 0.699 mmol) in tetrahydrofuran (4 ml) was added to a solution of lithium aluminum hydride (53 mg, 1.40 mmol) in tetrahydrofuran (4 ml) at room temperature, and the resulting mixture was refluxed for 2 hours. Subsequently, water (0.053 ml), a 2N-aqueous lithium hydroxide solution (0.106 ml) and water (0.212 ml) were added in that order to the reaction solution and stirred, followed by filtration. The solvent was distilled off under reduced pressure and the residue was dried under reduced pressure to obtain 1-(1H-indazol-5-yl)methanamine (97 mg, 94%).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. filtrationfollowed by filtration
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-68d13fd7f8224947a4bbf1878f118c03
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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