Ammonia → CID 14590535

HRID 1658757Notes

Reaction equation

HRID 1658757 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:21][CH2:22][CH3:23])=[C:8]2[CH:14]=[N:13][N:12](CC3OC=CC=3)[C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].[Se](=O)=O.O.N>COCCOCCOC.O.CO>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:21][CH2:22][CH3:23])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 24007Selenium DioxideHCID 544738334-Ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 14590535CID 14590535Yield 67%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8150DiglymeSolvent

Procedure

31.5 g of 4-ethoxy-1-(2-furyl)methyl-1H-pyrazolo[3,4-b]pyridine- 5-carboxylic acid ethyl ester (0.1 mol) and 20 g of selenium dioxide (0.18 mol) are suspended in 100 ml diethyleneglycol dimethylether. The mixture is heated with stirring at 160° and a few drops of water are added. The temperature is held steady for 1.5 hours. After cooling, 100 ml of water is added and the mixture is neutralized with a dilute solution of aqueous ammonia. Yellow crystals are formed, which yield on recrystallization from methanol 15.8 g of 4-ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (67%), m.p. 180°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureAfter cooling
  3. customYellow crystals are formed

Sources & evidence

ORD record
ord-16f2dcabb9374c01b4df26d5d725e84e
Source dataset
uspto-grants-1976_06
Patent number
US03966746

Reaction notes

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