Ammonium Chloride → HCID 67974925, compound

HRID 706655Notes

Reaction equation

HRID 706655 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([N+:20]([O-])=O)[CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)[CH3:2].[Cl-].[NH4+]>[Fe].CCO.O>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:20])[C:14]=3[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67976364HCID 67976364, compound

Product 1

HCID 67974925HCID 67974925, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 1-((6-ethoxypyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (0.118 g, 0.378 mmol), ammonium chloride (0.0101 g, 0.189 mmol) in 4:1 EtOH/water (2 mL) was treated with iron (0.211 g, 3.78 mmol) and refluxed for 2 hours. The solvent was removed and the residue taken in EtOAc-water and filtered through glass fiber filter paper. The organic phase was separated, dried (phase separator silicone treated filter paper), and concentrated to provide 1-((6-ethoxypyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine (0.076 g, 71% yield) as a yellow gum.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was removed
  3. filtrationfiltered through glass fiber
  4. filtrationfilter paper
  5. customThe organic phase was separated
  6. customdried
  7. addition(phase separator silicone treated filter paper)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1f317b418c6a499e865a443c815d7e6b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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