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

HRID 552824
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HRID 552824 반응식
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
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참가 물질

4

반응물 2

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

생성물 1

HCID 4225291H-indazole-6-carbonitrile수율 56%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

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후처리

  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)

출처 및 근거

ORD 기록
ord-319e697a428140c4b25870b77fc86ba5
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951825B2

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