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

HRID 656852ノート

反応式

HRID 656852 の反応式
[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

参加物

6

反応物 3

HCID 14797Potassium Hydroxide2 回HCID 312751,4-DioxaneHCID 68811156HCID 68811156、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5c9fc23cbc054d5ab5afaa8403100b84
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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