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

HRID 234822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234822
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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1ab01fa438ec4a2eb259307d9c283e7f
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596097

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