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

HRID 638301

Reaction equation

HRID 638301 reaction equation
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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-fe0cb3eede804bada742cb29242fa3fe
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Linked notes

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