Ammonium Chloride → HCID 86694716, compound

HRID 475168Notes

Reaction equation

HRID 475168 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([C:12](=[N:14]O)[CH3:13])[CH:3]=1.[NH4+].[Cl-]>CO.[Zn]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([CH:12]([NH2:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 136336869HCID 136336869, compound

Product 1

HCID 86694716HCID 86694716, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To the solution of 1-(6-fluoro-1-methyl-1H-indazol-4-yl)ethanone oxime (848 mg, 4.10 mmol) in MeOH (60 mL) was added powdered Zn (13.6 g, 212.5 mmol, 50.0 eq.) and NH4Cl (13.6 g, 251 mmol, 60.0 eq.). The mixture was heated at reflux overnight, filtered, and concentrated in vacuo. To the residue was added DCM, and the mixture was washed with water, dried (MgSO4) and concentrated in vacuo to afford 1-(6-fluoro-1-methyl-1H-indazol-4-yl)ethanamine (131) as syrup (785 mg, 87%). MS (ESI): m/z=177.2 [M−NH2]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionTo the residue was added DCM
  6. washthe mixture was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57b4ff46258d4b7eb5640d79dcbec7f2
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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