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

HRID 654373Notes

Reaction equation

HRID 654373 reaction equation
[I:1]I.[CH2:3]([C:5]1[CH:14]=[C:13]([O:15]CC2C=CC(B(O)O)=CC=2)[C:12]2CC[CH2:9][CH2:8][C:7]=2[N:6]=1)[CH3:4].[OH-].[Na+]>O>[CH2:8]([C:7]1[NH:6][C:5]([CH2:3][CH3:4])=[CH:14][C:13](=[O:15])[C:12]=1[I:1])[CH3:9]

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acid

Product 1

HCID 149504792,6-diethyl-3-iodo-4(1H)-pyridoneYield 75.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodine (720 mg) was added to a solution of compound C (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 (D) (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-7a45fdeb47f94efa90227a979fd0aac4
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

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