Ammonium Chloride → HCID 67974138, compound

HRID 706645Notes

Reaction equation

HRID 706645 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>[Fe].CCO.O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH3:20])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 679761361-benzyl-3-methyl-4-nitro-1H-indazole

Product 1

HCID 67974138HCID 67974138, compoundYield 1,020.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 1-benzyl-3-methyl-4-nitro-1H-indazole (0.052 g, 0.19 mmol), ammonium chloride (0.0052 g, 0.097 mmol) in 4:1 EtOH/water (5 mL) was treated with iron (0.11 g, 1.9 mmol) and refluxed for 2 hours. The mixture was concentrated and residue shaken in EtOAc/water, filtered through GF/F paper, and concentrated to provide 1-benzyl-3-methyl-1H-indazol-4-amine (0.46 g, 82% yield) as a yellow gum.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered through GF/F paper
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8af751a424724879a959b39aa23e4079
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…