Water → HCID 18447080, compound

HRID 1269797Notes

Reaction equation

HRID 1269797 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#[N:21])=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]3[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=3[CH2:20][NH2:21])=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22933852HCID 22933852, compound

Product 1

HCID 18447080HCID 18447080, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (44 mg, 1.12 mmol) was added to a solution of the 2-[(1H-indazol-5-yloxy)methyl]benzonitrile (70 mg, 0.281 mmol) obtained in Example 346 in tetrahydrofuran (8 ml), and the resulting mixture was refluxed. After 2 hours, water, a 2M-aqueous sodium hydroxide solution and then water were added to the reaction mixture, and the resulting solution was filtered by the use of Celite. The filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1% aqueous ammonia)) to obtain 2-[(1H-indazol-5-yloxy)methyl]benzyl-amine (52 mg, 74%).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. filtrationthe resulting solution was filtered by the use of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1% aqueous ammonia))

Sources & evidence

ORD record
ord-0af4b2c414904e7fae308bbc68a8a9b6
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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