Aluminum(III) Chloride → 9-Fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione

HRID 234808노트

반응식

HRID 234808 반응식
[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[N:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:17])[C:6]=2[C:5]([O:18]C)=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl.[Cl-].[Na+].O>[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[CH:12]=[N:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:17])[C:6]=2[C:5]([OH:18])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 6451240Aluminum(III) Chloride2회HCID 104913596-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

생성물 1

HCID 105143529-Fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione수율 102.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

A mixture of 9-fluoro-6-methoxybenzo[g]isoquinoline-5,10-dione (0.072 g) and aluminum trichloride (0.112 g) in dry methylene chloride (40 mL) is stirred at room temperature for 4 hours under a nitrogen atmosphere. An additional portion of aluminum chloride (0.190 g) is added and the mixture is allowed to react at reflux for 1.5 hrs and at room temperature overnight. Following addition of brine (15 mL) the aqueous phase is separated and extracted with methylene chloride (3×5 mL). The combined organic solutions are dried over anhydrous sodium sulphate and the solvent is removed by distillation at reduced pressure to give an approximately 1:1 mixture (0.070 g) of 9-fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione (slower moving yellow spot on silica gel TLC plate, eluant methylene chloride/ethyl acetate 70/30) and 9-chloro-6-hydroxybenzo[g]isoquinoline-5,10-dione (faster moving yellow spot on the above chromatographic system) which is used without further purification for the next step.

후처리

  1. customto react
  2. temperatureat reflux for 1.5 hrs and at room temperature overnight
  3. customis separated
  4. extractionextracted with methylene chloride (3×5 mL)
  5. dry with materialThe combined organic solutions are dried over anhydrous sodium sulphate
  6. customthe solvent is removed by distillation at reduced pressure

출처 및 근거

ORD 기록
ord-38bc3982e19d4bd391f75be4d9973282
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596097

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