Isatin → 2-(3,4-Difluorophenyl)-4-quinolinecarboxylic acid

HRID 411514

反応式

HRID 411514 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[C:2]1=[O:11].[F:12][C:13]1[CH:14]=[C:15]([C:20](=O)[CH3:21])[CH:16]=[CH:17][C:18]=1[F:19].[OH-:23].[K+]>O1CCOCC1>[F:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:3]([C:2]([OH:11])=[O:23])[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]=2)[CH:16]=[CH:17][C:18]=1[F:19]

参加物

5

反応物 3

HCID 7054IsatinHCID 14797Potassium HydroxideHCID 1230521-(3,4-Difluorophenyl)ethan-1-one

生成物 1

HCID 46116332-(3,4-Difluorophenyl)-4-quinolinecarboxylic acid収率 5.3%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

A mixture of 2,3-indolinedione (5 g, 0.03 mole), 3′,4′-difluoroacetophenone (5 g, 0.03 mole) and potassium hydroxide (3 g, 0.05 mole) in 1,4-dioxane (50 mL) is heated at 105° C. for 48 hours. The reaction solution is then cooled to room temperature and concentrated under reduced pressure. The residue is treated with EtOAc and extracted with water. The pH of the aqueous layer is adjusted to 5-6 with 1N HCl, the resulting solid is collected by vacuum filtration, washed with water, and dried to give the titled compound (450 mg) as a yellow solid.

後処理

  1. temperatureThe reaction solution is then cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is treated with EtOAc
  4. extractionextracted with water
  5. filtrationthe resulting solid is collected by vacuum filtration
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-ba1a3861c38f4b82a8002ce411707de2
出典データセット
uspto-grants-2003_05
特許番号
US06559163B2

関連ノート

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