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

HRID 234808Notes

Reaction equation

HRID 234808 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-38bc3982e19d4bd391f75be4d9973282
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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