Methyl iodide → 2-Ethylquinoline

HRID 33775

Reaction equation

HRID 33775 reaction equation
C(NC(C)C)(C)C.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[N:13]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=CC=1C.CI>C1COCC1>[CH2:11]([C:10]1[CH:9]=[CH:17][C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:13]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 70602-MethylquinolineHCID 7912DiisopropylamineHCID 178418339Butyllithium

Product 1

HCID 1371132-Ethylquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 0.40 M solution of diisopropyl amine in THF at −10° C. was added slowly 1.0 equiv of a solution of n-BuLi (2.5 M/hexane). After 10 min, the mixture was cooled to −78° C. and 0.9 equiv of quinaldine was added dropwise. The red/orange solution was then stirred at 0° C. for 1 h. MeI was then added and the reaction was stirred at room temperature for 2 h. The reaction was quenched with aqueous NH4Cl solution, and then extracted with EtOAc. The organic phase was washed with H2O and brine. The solution was then dried (MgSO4), filtered, and evaporated. The crude material was purified by flash chromatography with 1:10 EtOAc:hexanes to give the title compound as a pale yellow oil.

Workup

  1. stirringthe reaction was stirred at room temperature for 2 h
  2. customThe reaction was quenched with aqueous NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialThe solution was then dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude material was purified by flash chromatography with 1:10 EtOAc

Sources & evidence

ORD record
ord-b46e68255d4c420991e21cad2ba93f5c
Source dataset
uspto-grants-2008_09
Patent number
US07429666B2

Linked notes

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