7-methoxy-8-nitroisoquinolin-1(2H)-one → 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577488
[CH3:1][O:2][C:3]1[C:12]([N+:13]([O-])=O)=[C:11]2[C:6]([CH:7]=[CH:8][NH:9][C:10]2=[O:16])=[CH:5][CH:4]=1>[Pd].C(O)C>[NH2:13][C:12]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:16])[NH:9][CH2:8][CH2:7]2

Komponenten

4

Edukt 1

HCID 867237137-methoxy-8-nitroisoquinolin-1(2H)-one

Produkt 1

HCID 867237148-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of 7-methoxy-8-nitroisoquinolin-1(2H)-one (296b, 30 g, 0.136 mol) and 10% palladium on carbon (15 g, 0.014 mol) in ethanol (1 L) was stirred at 40° C. under hydrogen (20 psi) for 72 hours. The mixture was filtered through celite, the flask and filter pad washed with ethanol (1 L), and the combined filtrates concentrated under vacuum to give 8-amino-7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (296c, 24 g, 92% yield) as a brown oil. MS: 193 [M+1].

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. filtrationthe flask and filter pad
  3. washwashed with ethanol (1 L)
  4. concentrationthe combined filtrates concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-340f148ea57746c49413a3ef3ac0ffbc
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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