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

HRID 234811

반응식

HRID 234811 반응식
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

참가 물질

8

반응물 4

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

생성물 2

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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 14b (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]iso quinoline-5,10-dione respectively (8.85 g).

후처리

  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

출처 및 근거

ORD 기록
ord-e2c2bbc75c0841fbbc9018ec4040fd67
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596097

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