4-Toluenesulfonyl chloride → 9-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

HRID 234810Notes

Reaction equation

HRID 234810 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]([OH:18])=[CH:4][CH:3]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(O)=CC=1.[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.C(N(CC)CC)C>N1C=CC=CC=1>[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][S:43]([C:40]2[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=2)(=[O:45])=[O:44])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 105143529-Fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dioneHCID 107777069-Chloro-6-hydroxybenzo[g]isoquinoline-5,10-dione

Product 1

HCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 1:1 mixture of 9-fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione and 9-chloro-6-hydroxybenzo[g]isoquinoline-5,10-dione, of Preparative Example 14a, (0.060 g) is dissolved in dry pyridine (2 mL) and p-toluenesulfonyl chloride (0.095 g) is added. After stirring at room temperature for one hour, triethylamine (0.25 mL) is added and stirring is continued for one additional hour. The reaction mixture is concentrated almost to dryness and partitioned between 1 N HCl (4 mL)-20% ammonium sulfate (6 mL) and ethyl acetate (10 mL). The aqueous phase is separated, extracted with ethyl acetate (3×5 mL) and discarded. The combined organic solutions are dried over anhydrous sodium sulphate and concentrated to dryness to give an approximately 1:1 mixture (0.095 g) of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione which is sued without further purification for the next step.

Workup

  1. stirringstirring
  2. concentrationThe reaction mixture is concentrated almost to dryness
  3. custompartitioned between 1 N HCl (4 mL)-20% ammonium sulfate (6 mL) and ethyl acetate (10 mL)
  4. customThe aqueous phase is separated
  5. extractionextracted with ethyl acetate (3×5 mL)
  6. dry with materialThe combined organic solutions are dried over anhydrous sodium sulphate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3cb06eb6ced24b909d2df5ffbeae5a98
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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