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

HRID 411514

반응식

HRID 411514 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
105 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ba1a3861c38f4b82a8002ce411707de2
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559163B2

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