Selenium Dioxide → HCID 178469709, compound

HRID 1576094Notes

Reaction equation

HRID 1576094 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[N:13][N:12](CC3C=CN=CC=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].[Se](=O)=[O:23]>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:23])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 867336054-picolyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 178469709HCID 178469709, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 176Acetic AcidSolvent

Procedure

3 g of 4-hydroxy-1-(4-picolyl-1H-pyrazolo[3,4-b]pyridine- 5-carboxylic acid ethyl ester (0.01 mol) is dissolved in 20 ml of acetic acid, 2.2 g of selenium dioxide (0.02 mol) and 2-3 drops of water are added. The mixture is refluxed for 30 minutes and then filtered off. 4-Hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester precipitates on cooling. Recrystallization from acetic acid yields 1.8 g (87%), m.p. 275°.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. filtrationfiltered off
  3. custom4-Hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester precipitates
  4. temperatureon cooling
  5. customRecrystallization from acetic acid
  6. customyields 1.8 g (87%), m.p. 275°

Sources & evidence

ORD record
ord-890e0be109b14d0093873c833a9dbd32
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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