Acetic Acid → HCID 178434470, compound

HRID 1943871Notes

Reaction equation

HRID 1943871 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.O.[N+:9]([CH:12]([CH:15]=O)[CH:13]=O)([O-:11])=[O:10].[Na].CC(O)=O>O>[CH3:1][C:2]1[C:6]2[C:5](=[N:7][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:15]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 71317419Sodium nitromalonaldehyde hydrateHCID 178418690HCID 178418690, compound

Product 1

HCID 178434470HCID 178434470, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 5 mL reaction vessel was charged with 3-methyl-1H-pyrazol-5-amine (68 mg, 0.70 mmol), sodium nitromalonaldehyde monohydrate (121 mg, 0.77 mmol) and AcOH (2 mL). The flask was heated to 90° C. under a nitrogen atmosphere overnight. The following day the mixture was poured into water (10 mL), and the precipitate was filtered and rinsed with water (3×5 mL). The precipitate was triturated with minimal Et2O to provide 3-methyl-5-nitro-1H-pyrazolo[3,4-b]pyridine as a solid (65 mg, 52% yield).

Workup

  1. customA 5 mL reaction vessel
  2. filtrationthe precipitate was filtered
  3. washrinsed with water (3×5 mL)
  4. customThe precipitate was triturated with minimal Et2O

Sources & evidence

ORD record
ord-3c7f71f284a04225b36f45bc5b7af167
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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