Sodium nitromalonaldehyde hydrate → HCID 178526792, compound

HRID 1943906Notes

Reaction equation

HRID 1943906 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:11]=[C:10]([NH2:12])[NH:9][N:8]=1.O.[N+:14]([CH:17]([CH:20]=O)[CH:18]=O)([O-:16])=[O:15].[Na]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]2[C:10](=[N:12][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:20]=2)[NH:9][N:8]=1

Participants

4

Reactant 2

HCID 71317419Sodium nitromalonaldehyde hydrateHCID 178507285HCID 178507285, compound

Product 1

HCID 178526792HCID 178526792, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 50 mL reaction vessel was charged with 3-(pyridin-2-yl)-1H-pyrazol-5-amine (1.5 g, 9.4 mmol), sodium nitromalonaldehyde monohydrate (1.54 g, 9.8 mmol) and water (9 mL). The flask was heated to 100° C. overnight, and the cooled reaction mixture was extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (MgSO4), to provide crude 3-(pyridin-2-yl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (2.0 g, 88% yield) as a solid.

Workup

  1. customA 50 mL reaction vessel
  2. customthe cooled reaction mixture
  3. extractionwas extracted with ethyl acetate (3×25 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-b44fe48e8fa64da1a51aecc11d3b763b
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…