Allyl iodide → 10-(2-Propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium Iodide

HRID 656913Notes

Reaction equation

HRID 656913 reaction equation
[O:1]1[C:14]2[C:13]3[N:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[CH2:15]([I:18])[CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[I-:18].[CH2:17]([N+:12]1[C:13]2[C:14]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:6]=[CH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1)[CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 11166Allyl iodide2×HCID 689964692,3-Dihydro[1,4]dioxino[2,3-h]quinoline

Product 1

HCID 6899119510-(2-Propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium IodideYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Dihydro[1,4]dioxino[2,3-h]quinoline (3.65 g; 19.52 mmol) and allyl iodide (6.52 ml; 39.04 mmol) were refluxed in toluene (50 ml) at 100° C. After 2.5 h more allyl iodide (0.65 ml; 3.9 mmol) was added to the mixture and the reaction continued under the same conditions for a further 0.5 h. The solvent was removed and the tar like product washed with toluene. This was dried under high vacuum overnight to afford the desired product (5.91 g; 85%).

Workup

  1. customThe solvent was removed
  2. washthe tar like product washed with toluene
  3. customThis was dried under high vacuum overnight

Sources & evidence

ORD record
ord-96f54fb39bca4ce888b0d6a92af84341
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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