Iodine → 5-Iodo-4-methyl-3-nitro-1,2-dihydropyridin-2-one

HRID 1387278Notes

Reaction equation

HRID 1387278 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].II.[I:14]([O-])(=O)=O.[Na+].O>C(O)(=O)C.S(=O)(=O)(O)O>[I:14][C:7]1[C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[C:4](=[O:8])[NH:5][CH:6]=1

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 3453702-Hydroxy-4-methyl-3-nitropyridineHCID 23675764Sodium Iodate

Product 1

HCID 217065145-Iodo-4-methyl-3-nitro-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-methyl-3-nitro-2-pyridone (2.00 g, 13 mmol) in acetic acid (12 mL) and concentrated sulfuric acid (1.6 ml,) was added iodine (1.32 g) and sodium iodate (0.55 g). The mixture was heated at 75° C. for 2.5 hours and then stirred at rt overnight. Water (100 mL) was added, and the precipitated 5-iodo-4-methyl-3-nitro-2-pyridone was collected by filtration (2.97 g, 82%).

Workup

  1. filtrationthe precipitated 5-iodo-4-methyl-3-nitro-2-pyridone was collected by filtration (2.97 g, 82%)

Sources & evidence

ORD record
ord-4e8af721267749e8b617049bd221cc3a
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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