Methylhydrazine → 5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one

HRID 234825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234825
[CH3:1][NH:2][NH2:3].[Cl:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[CH:15]=[N:14][CH:13]=[CH:12][C:11]=3[C:10](=O)[C:9]=2[C:8](F)=[CH:7][CH:6]=1>N1C=CC=CC=1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]2[N:2]([CH3:1])[N:3]=[C:10]3[C:11]4[CH:12]=[CH:13][N:14]=[CH:15][C:16]=4[C:17](=[O:19])[C:18]=1[C:9]=23

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 108490269-Chloro-6-fluorobenzo[g]isoquinoline-5,10-dione

Produkt 1

HCID 199747705-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

A solution of methyl hydrazine (0.76M; 0.021 g) in pyridine (0.6 mL) is added dropwise over two min to a stirred solution of 9-chloro-6-fluoro benzo[g]isoquinoline-5,10-dione of Preparative Example 20 in pyridine (0.5 mL) cooled with an ice-bath. A yellow precipitate appears in the dark solution after 6 min. After 1.3 h the reaction mixture is reduced to half its volume by a gentle stream of nitrogen and quenched with ice (5 g). The pale yellow precipitate is collected by suction filtration and washed with ice-water (2×1 mL) and dried under vacuum. The yellow solid is purified by silica gel column chromatography (eluant: chloroform/methanol 96/4 v/v) to yield 5-chloro-2-methylisoquino[5,6,7-cd]indazole-6(2H)-one (0.033 g; 71% yield) as a yellow solid.

Aufarbeitung

  1. temperaturecooled with an ice-bath
  2. waitAfter 1.3 h the reaction mixture is reduced to half its volume by a gentle stream of nitrogen
  3. customquenched with ice (5 g)
  4. filtrationThe pale yellow precipitate is collected by suction filtration
  5. washwashed with ice-water (2×1 mL)
  6. customdried under vacuum
  7. customThe yellow solid is purified by silica gel column chromatography (eluant: chloroform/methanol 96/4 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-328cf988e0d645738455b34c8bc5bc94
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05596097

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