Iodoethane → HCID 86734967, compound

HRID 259405Notes

Reaction equation

HRID 259405 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:13][N:14]([CH3:16])[CH:15]=2)[N:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:17](I)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([N:5]1[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2](=[O:1])[C:3]2=[CH:15][N:14]([CH3:16])[N:13]=[C:4]12)[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469710HCID 178469710, compound

Product 1

HCID 86734967HCID 86734967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.1 g. of 4-hydroxy-2-methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester (0.1 mol.), 17.1 g. of ethyl iodide and 21 g. of potassium carbonate (0.15 mol.) are stirred together in 200 ml. of dimethylformamide at 80° for 12 hours. The inorganic precipitate is filtered off and the filtrate evaporated to dryness. Recrystallization of the residue with ethyl acetate yields 18.2 g. of 7-ethyl-4,7-dihydro-2-methyl-4-oxo-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester, yield (73%); m.p. 170°-172°.

Workup

  1. filtrationThe inorganic precipitate is filtered off
  2. customthe filtrate evaporated to dryness
  3. customRecrystallization of the residue with ethyl acetate
  4. customyields 18.2 g

Sources & evidence

ORD record
ord-57c2f01d324440ff80efa3ef9e5fbf2b
Source dataset
uspto-grants-1977_07
Patent number
US04038281

Reaction notes

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