Water → HCID 10059638, compound

HRID 1110017Notes

Reaction equation

HRID 1110017 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([Li])CCC.[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>CCOCC.CCCCCC>[CH2:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 70602-MethylquinolineHCID 81011-BromohexaneHCID 178418339Butyllithium

Product 1

HCID 10059638HCID 10059638, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 25 g of 2-methylquinoline in 40 ml of ether was added slowly to a mixture of 70 ml of a 1.6M solution of n-butyllithium in hexane and 40 ml of diethyl ether. The reaction mixture was stirred at room temperature, then it was cooled to about 5° C. and a solution of 28.9 g of n-hexyl bromide in 10 ml of ether was slowly added. The reaction mixture was then warmed to room temperature and stirred at room temperature for 2 hours. For working-up, the reaction mixture was added to 500 ml of water and extracted with ether. The organic phase was washed with slightly acidified water, dried and evaporated. The crude product obtained was purified by chromatography on a silica gel column using dichloromethane as the eluent. 31 g of oily crude 2-n-heptylquinoline were obtained.

Workup

  1. temperatureit was cooled to about 5° C.
  2. temperatureThe reaction mixture was then warmed to room temperature
  3. stirringstirred at room temperature for 2 hours
  4. extractionextracted with ether
  5. washThe organic phase was washed with slightly acidified water
  6. customdried
  7. customevaporated
  8. customThe crude product obtained
  9. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-0e46494a11b441e0b4ddbd50ff86deec
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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