Allyl iodide → HCID 68811156, compound

HRID 656851Notes

Reaction equation

HRID 656851 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[CH2:13]([I:16])[CH:14]=[CH2:15]>C1(C)C=CC=CC=1>[I-:16].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N+:10]2[CH2:15][CH:14]=[CH2:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 11166Allyl iodide2×HCID 786667-Methoxyquinoline

Product 1

HCID 68811156HCID 68811156, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

7-(Methyloxy)quinoline (8.76 g; 55.09 mmol) and allyl iodide (19.72 ml; 110.18 mmol) were refluxed in toluene (120 ml) at 95° C. for 1 h, more allyl iodide (9.86 ml; 55.09 mmol) was added and the temperature of the reaction increased to 110° C. After a further 1 h the temperature of the reaction was increased to 120° C. and reaction continued for a further 0.5 h. The solvent was removed under vacuum and the resulting brown solid was washed with toluene and diethyl ether. The resultant solid were left to dry in a vacuum oven overnight to give the desired product (14.81 g; 82%)

Workup

  1. temperatureAfter a further 1 h the temperature of the reaction was increased to 120° C.
  2. customreaction
  3. customThe solvent was removed under vacuum
  4. washthe resulting brown solid was washed with toluene and diethyl ether
  5. waitThe resultant solid were left
  6. customto dry in a vacuum oven overnight

Sources & evidence

ORD record
ord-15d72a5f88124eb5a0b02bcf6a96b9ec
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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