Iodoethane → HCID 21421712, compound

HRID 259403Notes

Reaction equation

HRID 259403 reaction equation
[OH:1][C:2]1[C:3]2[C:4](=[N:16][N:17]([CH3:19])[CH:18]=2)[N:5]=[CH:6][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].[CH2:20](I)[CH3:21].[OH-].[Na+]>CN(C)C=O>[C:8]([C:7]1[C:2](=[O:1])[C:3]2[C:4](=[N:16][N:17]([CH3:19])[CH:18]=2)[N:5]([CH2:20][CH3:21])[CH:6]=1)(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 178479973HCID 178479973, compound

Product 1

HCID 21421712HCID 21421712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.3 g. of (4-hydroxy-2-methyl-2H-pyrazolo[3,4-b]pyridin-5-yl)phenylmethanone (0.1 mol.), 17.1 g. of ethyl iodide (0.11 mol.) and 5 g. of sodium hydroxide are heated together in 150 ml. of dimethylformamide for 12 hours with continuous stirring at 100°. The mixture is filtered hot, evaporated to dryness and the residue is recrystallized from butanol to obtain 5-benzoyl-7-ethyl-2,7-dihydro-2-methyl-4H-pyrazolo[3,4-b]pyridin-4-one, yield 20.3 g. (72%); m.p. 217°-218°.

Workup

  1. filtrationThe mixture is filtered hot
  2. customevaporated to dryness
  3. customthe residue is recrystallized from butanol

Sources & evidence

ORD record
ord-640934d6a7d1416aa95127dffcd9d769
Source dataset
uspto-grants-1977_07
Patent number
US04038281

Reaction notes

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