Iodine → HCID 20080870, compound

HRID 1653845Notes

Reaction equation

HRID 1653845 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:17])=[CH:5][C:6](=[O:16])[C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].II.[I:20](O)(=O)=O>C(O)C.O.S([O-])([O-])=O.[Na+].[Na+]>[I:20][C:5]1[C:6](=[O:16])[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:2]([CH3:1])[NH:3][C:4]=1[CH3:17]

Participants

7

Reactant 3

HCID 807IodineHCID 24345Iodic acidHCID 20080850HCID 20080850, compound

Product 1

HCID 20080870HCID 20080870, compoundYield 205.8%

Reagents, catalysts & solvents 3

HCID 24437Sodium SulfiteCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2,6-dimethyl-3-octylpyridin-4(1H)-one (1.17 g) and iodine (0.63 g) in ethanol (15 ml) at 70° was added dropwise a solution of iodic acid (0.22 g) in water (1 ml). After 30 min the mixture was allowed to cool and a few drops of an aqueous sodium sulphite solution added to remove excess iodine. The precipitate was filtered, washed with ethanol and recrystallised from DMF to give the title compound (0.93 g), m.p. 224°-226°, NMR δH (d6 -DMSO) 2.42 (3H, s), 2.3-2.5 (2H, m), 2.2 (3H, s), 1.1-1.45 (12H, m), 0.85 (3H, t).

Workup

  1. temperatureto cool
  2. customto remove excess iodine
  3. filtrationThe precipitate was filtered
  4. washwashed with ethanol
  5. customrecrystallised from DMF

Sources & evidence

ORD record
ord-d44528023ace432488e05cd283499db6
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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