Potassium Hydroxide → 7-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 656852Notes

Reaction equation

HRID 656852 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N+:11]2[CH2:14][CH:15]=[CH2:16])=[CH:6][CH:5]=1.[OH-].[K+].[O:19]1CCOCC1>O.CCOC(C)=O>[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10](=[O:19])[N:11]2[CH2:14][CH:15]=[CH2:16])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 312751,4-DioxaneHCID 68811156HCID 68811156, compound

Product 1

HCID 688097807-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinoneYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

7-(Methyloxy)-1-(2-propen-1-yl)quinolinium iodide (14.81 g; 45.43 mmol), KOH (11.20 g; 199.89 mmol) and K3-[Fe(CN)6] (32.78 g; 99.95 mmol) were stirred in 1:1 water: 1,4-dioxane (400 ml) at rt under Argon for 1 h. More KOH (1.1 g; 19.9 mmol) and K3-[Fe(CN)6] (3.28 g; 10.0 mmol) were added to the reaction and it was stirred under the same conditions for a further 0.5 h. EtOAc (500 ml) and water (500 ml) was then added. The layers were then separated and the combined organic layers were washed with water and then concentrated. The crude residue was then purified by column chromatography on silica gel using a 0-5% MeOH/DCM gradient to give the desired product (4.90 g; 51%).

Workup

  1. customThe layers were then separated
  2. washthe combined organic layers were washed with water
  3. concentrationconcentrated
  4. customThe crude residue was then purified by column chromatography on silica gel using a 0-5% MeOH/DCM gradient

Sources & evidence

ORD record
ord-5c9fc23cbc054d5ab5afaa8403100b84
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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