Allyl iodide → 6-Fluoro-10-(2-propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium Iodide

HRID 657016Notes

Reaction equation

HRID 657016 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:8]=2[C:9]2[O:15][CH2:14][CH2:13][O:12][C:10]=2[CH:11]=1.[CH2:16]([I:19])[CH:17]=[CH2:18]>C1(C)C=CC=CC=1>[I-:19].[F:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N+:7]([CH2:18][CH:17]=[CH2:16])[C:8]=2[C:9]2[O:15][CH2:14][CH2:13][O:12][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 11166Allyl iodideHCID 689933986-Fluoro-2,3-dihydro[1,4]dioxino[2,3-h]quinoline

Product 1

HCID 689912236-Fluoro-10-(2-propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium IodideYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-fluoro-2,3-dihydro[1,4]dioxino[2,3-h]quinoline (2.78 g, 13.6 mmol) and allyl iodide (2.5 ml, 27.2 mmol) in toluene (50 ml) under argon was heated at 90° C. than at 120° C. for 5 h. The reaction was cooled to rt, the solvent decanted and the solid dried in the vacuum oven at 40° C. overnight to afford the desired product (4 g, 80%).

Workup

  1. customthe solvent decanted
  2. customthe solid dried in the vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-ebde29b9ef2b485a86970b50960c3ff4
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

Loading…