m-Chloroperbenzoic acid → 9-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione-2-oxide

HRID 234815Notes

Reaction equation

HRID 234815 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[C:26]2[C:25](=[O:27])[C:24]3[CH:23]=[N:22][CH:21]=[CH:20][C:19]=3[C:18](=[O:28])[C:17]=2[C:16]([O:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:15][CH:14]=1>ClCCl>[F:12][C:13]1[C:26]2[C:25](=[O:27])[C:24]3[CH:23]=[N+:22]([O-:6])[CH:21]=[CH:20][C:19]=3[C:18](=[O:28])[C:17]=2[C:16]([O:29][S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Product 1

HCID 233555479-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione-2-oxideYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 3-chloroperoxybenzoic acid (3.92 g; 55% titre) in dichloromethane (50 mL) is dropped during 5 min into a mixture of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione (1.98 g) in dichloromethane (20 mL). Care is taken to avoid the addition of the aqueous layer that separates from the dichloromethane solution of 3-chloroperoxybenzoic acid. An exothermic reaction ensues, and at the end of the addition the mixture is refluxed overnight. After cooling to room temperature the reaction mixture is diluted with dichloromethane (50 mL) and the organic solution is washed with water (3×30 mL). After drying over sodium sulfate the organic solution is concentrated to a volume of about 20 mL, diluted with absolute ethanol (30 mL) and concentrated to a small volume. After stirring at 0° C. for 1 h a yellow solid separates which is filtered, to give 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione-2-oxide (1.35 g).

Workup

  1. customAn exothermic reaction
  2. additionat the end of the addition the mixture
  3. temperatureis refluxed overnight
  4. washthe organic solution is washed with water (3×30 mL)
  5. dry with materialAfter drying over sodium sulfate the organic solution
  6. concentrationis concentrated to a volume of about 20 mL
  7. additiondiluted with absolute ethanol (30 mL)
  8. concentrationconcentrated to a small volume
  9. filtrationis filtered

Sources & evidence

ORD record
ord-0551d63fbc9343f7a5045b6f7a0c18ed
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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