Iodine → 4-Chloro-6-methyl-2-(4-methylphenyl)quinoline

HRID 638301

반응식

HRID 638301 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.II.[OH-].[Na+]>CCOCC.CCCCCC.O>[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH3:25])[CH:23]=2)[N:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[CH:16]=1

참가 물질

9

반응물 5

HCID 807IodineHCID 78054-BromotolueneHCID 14798Sodium HydroxideHCID 8246244-Chloro-6-methylquinolineHCID 178418339Butyllithium

생성물 1

HCID 136039044-Chloro-6-methyl-2-(4-methylphenyl)quinoline

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

To a solution of 4.3 g (25 mmol) of p-bromotoluene in 50 ml of ether cooled to 5° was dropwise added 15 ml of a 1.6M solution of butyl lithium in hexane, while maintaining the temperature below 5°. This mixture was stirred at 5° for 10 min and at 30° for 10 min. and then cooled to -20°. A solution of 4.0 g (22 mmol) of 4-chloro-6-methylquinoline, prepared as in Example 25, in 20 ml of ether was added while maintaining the temperature at -20°. It was then allowed to stir at room temperature for 15 min. To the reaction mixture was then added 10 ml of water and 5 g of iodine, and 60 ml of 3N sodium hydroxide. After 20 min of stirring the organic layer was separated. The aqueous phase was extracted with an equal volume of ether. The organic phases were combined, washed with water, dried over sodium sulfate, and concentrated in vacuo to leave the above-named 4-chloroquinoline as a yellow oil. A solution of this oil in methylene chloride was filtered through a plug of alumina. The filtrate was concentrated in vacuo to give 3.22 g of the above-named product, mp 40°-50°.

후처리

  1. temperaturewhile maintaining the temperature below 5°
  2. temperaturecooled to -20°
  3. temperaturewhile maintaining the temperature at -20°
  4. stirringto stir at room temperature for 15 min
  5. stirringAfter 20 min of stirring the organic layer
  6. customwas separated
  7. extractionThe aqueous phase was extracted with an equal volume of ether
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fe0cb3eede804bada742cb29242fa3fe
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560692

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