Methylhydrazine → 2-methyl-5-(p-toluenesulfonyloxy)isoquino [8,7,6-cd]indazole-6(2H)-one

HRID 234822

반응식

HRID 234822 반응식
F[C:2]1[C:15]2[C:14](=O)[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:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1.ClC1C2C(=O)C3C=NC=CC=3C(=O)C=2C(OS(C2C=CC(C)=CC=2)(=O)=O)=CC=1.[CH3:57][NH:58][NH2:59]>N1C=CC=CC=1>[CH3:57][N:58]1[C:2]2[CH:3]=[CH:4][C:5]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[C:6]3[C:7](=[O:17])[C:8]4[CH:9]=[CH:10][N:11]=[CH:12][C:13]=4[C:14]([C:15]=23)=[N:59]1

참가 물질

5

반응물 3

HCID 6061MethylhydrazineHCID 105728809-Fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dioneHCID 199747549-Chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione

생성물 1

HCID 153378742-methyl-5-(p-toluenesulfonyloxy)isoquino [8,7,6-cd]indazole-6(2H)-one

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

The 1:1 mixture of 9-fluoro-6-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione and 9-chloro-6-(p-toluenesulfonyloxy)benzo[g]isoquino line-5,10-dione, of Preparative Example 15a, (0.041 g) is dissolved in dry pyridine (2 mL) and a freshly prepared 1M solution of N-methyhydrazine in pyridine (0.183 mL) is added. After stirring for three hours at room temperature the reaction mixture is concentrated to dryness and added with water (5 mL), with NaH2PO4 saturated solution (5 mL) and extracted several times with methylene chloride (50 mL). The combined organic solutions are dried ever anhydrous sodium sulfate and the solvent is removed at reduced pressure. The obtained residue is purified by silica-gel column chromatography (eluant: methylene chloride/ethyl acetate 90/10 v/v (50 mL), then 75/25 (50 mL), then 60/40 (50 mL) and finally 40/60 (50 mL) to give 2-methyl-5-(p-toluenesulfonyloxy)isoquino[8,7,6-cd]indazole-6(2H)-one.

후처리

  1. concentrationis concentrated to dryness
  2. additionadded with water (5 mL), with NaH2PO4 saturated solution (5 mL)
  3. extractionextracted several times with methylene chloride (50 mL)
  4. dry with materialThe combined organic solutions are dried ever anhydrous sodium sulfate
  5. customthe solvent is removed at reduced pressure
  6. customThe obtained residue is purified by silica-gel column chromatography (eluant

출처 및 근거

ORD 기록
ord-1ab01fa438ec4a2eb259307d9c283e7f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596097

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