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

HRID 234810노트

반응식

HRID 234810 반응식
[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

참가 물질

6

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 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3cb06eb6ced24b909d2df5ffbeae5a98
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596097

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