Iodoethane → CID 14590535

HRID 1576095Notes

Reaction equation

HRID 1576095 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:15])=[C:8]2[CH:14]=[N:13][NH:12][C:9]2=[N:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:15][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

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469709HCID 178469709, compound

Product 1

HCID 14590535CID 14590535

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.1 g of 4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (0.02 mol), 5.6 g of potassium carbonate (0.04 mol) and 3.5 g of ethyl iodide (0.022 mol) are heated in 30 ml of dimethylformamide with stirring for 10 hours at 60°. After this time, the excess potassium carbonate is filtered off and 30 ml of water is added. 4-Ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester precipitates and is recrystallized from methanol, yield 2 g (42.5%), m.p. 180°.

Workup

  1. filtrationAfter this time, the excess potassium carbonate is filtered off
  2. addition30 ml of water is added
  3. custom4-Ethoxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester precipitates
  4. customis recrystallized from methanol, yield 2 g (42.5%), m.p. 180°

Sources & evidence

ORD record
ord-4afdfe058b4c4aea91a34c21077390c8
Source dataset
uspto-grants-1976_09
Patent number
US03979399

Reaction notes

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