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

HRID 656852노트

반응식

HRID 656852 반응식
[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

참가 물질

6

반응물 3

HCID 14797Potassium Hydroxide2회HCID 312751,4-DioxaneHCID 68811156HCID 68811156, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5c9fc23cbc054d5ab5afaa8403100b84
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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