Sodium Carbonate → 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile

HRID 1595759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595759
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[NH2:20][C:21]1[CH:22]=[C:23]2[C:28](=[O:29])[NH:27][C:25](=[O:26])[C:24]2=[CH:30][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:26]=[C:25]1[C:24]2[C:23](=[CH:22][C:21]([NH:20][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:18]#[N:19])=[CH:31][CH:30]=2)[C:28](=[O:29])[NH:27]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 729154-AminophthalimideHCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Produkt 1

HCID 98012214-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrileAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 305 mg (1.88 mM) of 4-Aminophthalimide in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100° C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80° C. to yield 348 mg of 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp=248-251° C.

Aufarbeitung

  1. customThe solid was collected
  2. washwashed with water
  3. customdried under vacuum at 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-954fac5e18e04e75b15ee0d00cf77395
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288082B1

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