Water → 10-(2-propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-9(10H)-one

HRID 656914Notes

Reaction equation

HRID 656914 reaction equation
[I-].[CH2:2]([N+:5]1[C:14]2[C:13]3[O:15][CH2:16][CH2:17][O:18][C:12]=3[CH:11]=[CH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH:3]=[CH2:4].[OH-:19].[K+].O>O1CCOCC1>[CH2:2]([N:5]1[C:14]2[C:13]3[O:15][CH2:16][CH2:17][O:18][C:12]=3[CH:11]=[CH:10][C:9]=2[CH:8]=[CH:7][C:6]1=[O:19])[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 6899119510-(2-Propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium Iodide

Product 1

HCID 6899122910-(2-propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-9(10H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10-(2-Propen-1-yl)-2,3-dihydro[1,4]dioxino[2,3-h]quinolin-10-ium iodide (5.91 g; 16.65 mmol), KOH (4.10 g; 73.26 mmol) and K3-[Fe(CN)6] (12.05 g; 36.63 mmol) were stirred in 50% aqueous 1,4-dioxane at RT for 1.5 h. Water (250 ml) was added and the aqueous layer was extracted with 10% MeOH/DCM (150 ml) and the organics were washed with water (250 ml). The organics were dried with MgSO4 and the solvents removed. The crude residues were purified by column chromatography on silica gel using a 0-7% MeOH/DCM gradient to give the desired product (2.6 g; 65%). MS (ES+) m/z 244 (MH+).

Workup

  1. extractionthe aqueous layer was extracted with 10% MeOH/DCM (150 ml)
  2. washthe organics were washed with water (250 ml)
  3. dry with materialThe organics were dried with MgSO4
  4. customthe solvents removed
  5. customThe crude residues were purified by column chromatography on silica gel using a 0-7% MeOH/DCM gradient

Sources & evidence

ORD record
ord-1039d1cfbede45de8f6618d984ce796e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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