Iodine → 2,6-diethyl-3-iodo-4(1H)-pyridone

HRID 1769076Notes

Reaction equation

HRID 1769076 reaction equation
[I:1]I.[CH2:3]([C:5]1[NH:6][C:7]([CH2:12][CH3:13])=[CH:8][C:9](=[O:11])[CH:10]=1)[CH3:4].[OH-].[Na+]>O>[CH2:3]([C:5]1[NH:6][C:7]([CH2:12][CH3:13])=[CH:8][C:9](=[O:11])[C:10]=1[I:1])[CH3:4]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 149504782,6-Diethylpyridin-4(1H)-one

Product 1

HCID 149504792,6-diethyl-3-iodo-4(1H)-pyridoneYield 36.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodine (720 mg) was added to a solution of compound F (430 mg) and sodium hydroxide (120 mg) in water (15 ml) and the mixture was stirred for 1 hour. The precipitated solid was collected by filtration and purified by flash chromatography, eluting with methanol/dichloromethane (1:19 v/v), to give 2,6-diethyl-3-iodo-4(1H)pyridone (G) (290 mg), m.p. 225°-227° C.; NMR (d6 -DMSO): 1.15(t, 6H), 2.5(q, 2H), 2.8(q, 2H), 5.9(s, 1H), 11.4(br s, 1H).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. custompurified by flash chromatography
  3. washeluting with methanol/dichloromethane (1:19 v/v)

Sources & evidence

ORD record
ord-d4b1b553c4424f56ba118ec77cb90a37
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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