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

HRID 1005412노트

반응식

HRID 1005412 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1119849fad054515802ec35d36299ce6
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054470

반응 노트

불러오는 중…