Nitric Acid → HCID 178434470, compound

HRID 930574Notes

Reaction equation

HRID 930574 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[N+:11]([O-])([OH:13])=[O:12].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>>[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178434440HCID 178434440, compound

Product 1

HCID 178434470HCID 178434470, compound

Procedure

3-Methyl-pyrazolo[3,4-b]pyridine (1 mmol, 1 eq.) was suspended into a mixture of 1:1 fuming nitric acid and concentrated sulfuric acid (1 mL:1 mL), and the resultant mixture was heated at 90° C. for 30 minutes. The reaction mixture was then cooled to rt, and poured into a mixture of sodium bicarbonate and ice. The resultant solution was warmed up to rt and extracted with 300 mL of EtOAc. The organic extract was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography to provide 70.2 mg of 3-methyl-5-nitro-pyrazolo[3,4-b]pyridine.

Workup

  1. extractionextracted with 300 mL of EtOAc
  2. extractionThe organic extract
  3. customwas separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c540c6131db041c4829b5f3e442636bd
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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