Lithium Chloride → 1-Hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone

HRID 1005412Notes

Reaction equation

HRID 1005412 reaction equation
[Cl-].[Li+].[CH2:3]([N:9]1[CH:14]=[C:13](I)[C:12]([CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[C:10]1=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:21]1([Sn](CCCC)(CCCC)CCCC)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.C(OCC)(=O)C>[CH2:3]([N:9]1[CH:14]=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]([CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[C:10]1=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 217065251-Hexyl-5-iodo-4-methyl-3-nitro-2-pyridone

Product 1

HCID 217065401-Hexyl-4-methyl-3-nitro-5-phenyl-2-pyridoneYield 72.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of bis(triphenylphosphine)Pd(II) chloride (0.014 g), lithium chloride (0.067 g), 1-hexyl-5-iodo-4-methyl-3-nitro-2-pyridone (0.15 g, 0.41 mmol) and phenyltributyltin (0.11 mL, 0.62 mmol) in THF (15 mL) was heated under reflux for 2 days. The mixture was cooled, diluted with ethyl acetate, and washed with aqueous potassium fluoride and water. The organic phase was dried, filtered and evaporated. Chromatography of the residue over silica gel (petroleum ether/methylene chloride 1/1 to methylene chloride gradient) gave 1-hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone (0.093 g, 72%). 3-Amino-1-hexyl-4-methyl-5-phenyl-2-pyridone. A mixture of 1-hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone (0.093 g, 0.30 mmol) and 10% Pd/C in ethyl acetate (100 mL) was hydrogenated at 45 psi in a Parr apparatus for 4 hours. The catalyst was removed by filtration, and the solvent was evaporated to give 3-amino-1-hexyl-4-methyl-5-phenyl-2-pyridone (0.083 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. temperatureThe mixture was cooled
  4. washwashed with aqueous potassium fluoride and water
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1119849fad054515802ec35d36299ce6
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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