Iodine → 2,6-diethyl-3-iodo-4(1H)-pyridone
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
Product 1
Reagents, catalysts & solvents 1
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
- filtrationThe precipitated solid was collected by filtration
- custompurified by flash chromatography
- washeluting with methanol/dichloromethane (1:19 v/v)
Sources & evidence
- ORD record
- ord-87392bc3cee9468cab6270681b4100ec
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05236936
Reaction notes
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