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

HRID 552824Notes

Reaction equation

HRID 552824 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 0.1M 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 0.1M 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-319e697a428140c4b25870b77fc86ba5
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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