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

HRID 234822ノート

反応式

HRID 234822 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ab01fa438ec4a2eb259307d9c283e7f
出典データセット
uspto-grants-1997_01
特許番号
US05596097

反応ノート

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