3-Amino-1H-indazole-6-carbonitrile → 1H-indazole-6-carbonitrile

HRID 2244614Notes

Reaction equation

HRID 2244614 reaction equation
N[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.N([O-])=O.[Na+]>CC(O)=O>[NH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[CH:2]=[N:3]1

Participants

4

Reactant 2

HCID 226152723-Amino-1H-indazole-6-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 4225291H-indazole-6-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 3-amino-1H-indazole-6-carbonitrile (345 mg) in AcOH was slowly added an aqueous NaNO2 solution (301 mg) at 0° C. It was stirred at room temperature for 2.5 days, and the residue was collected by filtration, and washed with cool water. To the residue were added 0.1 M HCl and DME, followed by stirring at 80° C. for 2 hours. The reaction mixture was neutralized with a saturated aqueous NaHCO3 solution, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20 to 50:50) to obtain 1H-indazole-6-carbonitrile (175 mg) as a yellow solid.

Workup

  1. filtrationthe residue was collected by filtration
  2. washwashed with cool water
  3. additionTo the residue were added 0.1 M HCl and DME
  4. stirringby stirring at 80° C. for 2 hours
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=80:20 to 50:50)

Sources & evidence

ORD record
ord-6c3c6916ae704f139b76ce3e26fd96b6
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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