ethyl 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate → Ethyl 8-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate

HRID 22978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22978
[NH2:1][S:2][O:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:12]2)=[CH:7][CH:6]=1.[H][H]>CN(C=O)C.[Pd]>[NH2:24][C:21]1[CH:22]=[CH:23][C:17]2[CH2:16][CH2:15][C:14]3[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:12][N:11]([C:8]4[CH:7]=[CH:6][C:5]([O:4][O:3][S:2][NH2:1])=[CH:10][CH:9]=4)[C:19]=3[C:18]=2[CH:20]=1

Komponenten

5

Edukt 2

HCID 22291943ethyl 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22592527Ethyl 8-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxylateAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The product of Example 2 (2.0 g) and 10% Pd/C (350 mg) in DMF (20 mL) were shaken at 55 psi hydrogen for 3 hours. The catalyst was removed by filtration and the filtrate was concentrated under vacuum to yield a yellow wax. The wax was triturated with methanol and the resulting amber solid was collected by filtration to afford the title compound (1.6 g).

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto yield a yellow wax
  4. customThe wax was triturated with methanol
  5. filtrationthe resulting amber solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-7085d5ffcae146b2aabcf5c3aaa406b0
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849653B2

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