Water → 5-nitro-1H-pyrazolo[3,4-b]pyridine

HRID 1943885Notes

Reaction equation

HRID 1943885 reaction equation
[NH:1]1[C:5]([NH2:6])=[CH:4][CH:3]=[N:2]1.O.[N+:8]([CH:11]([CH:14]=O)[CH:12]=O)([O-:10])=[O:9].[Na].O>C(O)(=O)C>[N+:8]([C:11]1[CH:12]=[C:4]2[CH:3]=[N:2][NH:1][C:5]2=[N:6][CH:14]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 74561Pyrazol-3-ylamineHCID 71317419Sodium nitromalonaldehyde hydrate

Product 1

HCID 123527765-nitro-1H-pyrazolo[3,4-b]pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1H-pyrazol-5-amine (0.804 g, 9.48 mmol) and sodium nitromalonaldehyde monohydrate (1.56 g, 9.96 mmol) in acetic acid (12 mL) was heated to 90° C. overnight. The reaction mixture was cooled to room temperature and poured into water (50 mL). The resulting solids were collected by filtration. The solids were washed with water (3×20 mL) and dried in vacuo to give 5-nitro-1H-pyrazolo[3,4-b]pyridine (1.40 g, 84%) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting solids were collected by filtration
  3. washThe solids were washed with water (3×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-62f08b78ecad40d3b8aac5dff32a4378
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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