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

HRID 440356

Reaction equation

HRID 440356 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[CH:19]=[N:18][CH:17]=[CH:16][C:15]=3[C:14](=[O:24])[C:13]=2[C:12]([OH:25])=[CH:11][CH:10]=1.[Cl:26][C:27]1[C:40]2[C:39](=[O:41])[C:38]3[CH:37]=[N:36][CH:35]=[CH:34][C:33]=3[C:32](=[O:42])[C:31]=2[C:30]([OH:43])=[CH:29][CH:28]=1.[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50](Cl)(=[O:52])=[O:51])=[CH:46][CH:45]=1>C(Cl)Cl.O>[F:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[CH:19]=[N:18][CH:17]=[CH:16][C:15]=3[C:14](=[O:24])[C:13]=2[C:12]([O:25][S:50]([C:47]2[CH:48]=[CH:49][C:44]([CH3:54])=[CH:45][CH:46]=2)(=[O:52])=[O:51])=[CH:11][CH:10]=1.[Cl:26][C:27]1[C:40]2[C:39](=[O:41])[C:38]3[CH:37]=[N:36][CH:35]=[CH:34][C:33]=3[C:32](=[O:42])[C:31]=2[C:30]([O:43][S:50]([C:47]2[CH:48]=[CH:49][C:44]([CH3:54])=[CH:45][CH:46]=2)(=[O:52])=[O:51])=[CH:29][CH:28]=1

Participants

8

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 2

HCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (8.20 mL) is added to a stirred suspension of the 9/1 mixture of 9-fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione and 9-chloro-6-hydroxybenzo[g]isoquinoline-5,10-dione respectively of Preparative Example 9b (5.53 g) and p-toluenesulfonylchloride (8.47 mL) in methylene chloride (166 mL). The reddish-violet solution obtained is left at room temperature under a nitrogen atmosphere for 1 hour and then it is poured into water (500 mL). The organic phase is separated and the aqueous solution is further extracted with methylene chloride (100 mL). The combined organic solutions are dried (Na2SO4) and concentrated to dryness. The obtained solid is suspended in n-hexane (100 mL) for 1 hour and filtered to give a 9:1 mixture (1H-NMR evaluation) of 9-fluoro-6-(p-toluenesulfonyloxy)benzo [g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione respectively (8.85 g).

Workup

  1. customThe reddish-violet solution obtained
  2. customThe organic phase is separated
  3. extractionthe aqueous solution is further extracted with methylene chloride (100 mL)
  4. dry with materialThe combined organic solutions are dried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. waitThe obtained solid is suspended in n-hexane (100 mL) for 1 hour
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2da9b8bb92ce42f98ee8e05ccdffcf57
Source dataset
uspto-grants-1996_05
Patent number
US05519029

Linked notes

Loading…