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

HRID 234808ノート

反応式

HRID 234808 の反応式
[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

参加物

5

反応物 2

HCID 6451240Aluminum(III) Chloride2 回HCID 104913596-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-38bc3982e19d4bd391f75be4d9973282
出典データセット
uspto-grants-1997_01
特許番号
US05596097

反応ノート

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