Ethylenediamine monohydrate → 5-Cyano-6-methoxy-2-methylthioquinoline

HRID 1825863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825863
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2.[C:16]([Cu])#[N:17].O.C(N)CN>CN(C=O)C>[C:16]([C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:14][CH3:15])=[N:7]2)#[N:17]

Komponenten

5

Edukt 3

HCID 12200817Ethylenediamine monohydrateHCID 221396965-Bromo-6-methoxy-2-methylthioquinolineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 221396835-Cyano-6-methoxy-2-methylthioquinolineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-bromo-6-methoxy-2-methylthioquinoline (6.1 g, 21 mmol) and CuCN (3.7 g, 41 mmol) in DMF (80 mL) was heated at 150° C. for 14 hours. The mixture was cooled and treated sequentially with 2:1 H2O/ethylenediamine (15 mL). The mixture was extracted with 1:1 EtOAc/hexane. The organic layer was worked-up. HPLC (1:8 EtOAc/hexane) gave 4.2 g (87%) of 5-cyano-6-methoxy-2-methylthioquinoline as a light yellow solid, (M+) 230(100).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with 1:1 EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2f18635a9b434c60b6b6ce07a7900912
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049325B2

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