Triethylamine → 2-Benzyloxy-5-cyano-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 278969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 278969
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:13]([O:20][N:21]1[C:30](=[O:31])[C:29]2[CH:32]=[C:33]([C:36]#[N:37])[C:34](Cl)=[C:27]3[C:28]=2[C:23](=[CH:24][CH:25]=[CH:26]3)[C:22]1=[O:38])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH2:13]([O:20][N:21]1[C:30](=[O:31])[C:29]2[CH:32]=[C:33]([C:36]#[N:37])[C:34]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:27]3[C:28]=2[C:23](=[CH:24][CH:25]=[CH:26]3)[C:22]1=[O:38])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 226240092-Benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione

Produkt 1

HCID 226239112-Benzyloxy-5-cyano-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dioneAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of pyrrolidine (0.070 g, 0.98 mmol) and triethyl amine (0.11 g, 1.1 mmol) in acetonitrile (5 mL) at reflux was added 2-benzyloxy-6-chloro-5-cyano-benzo[de]isoquinoline-1,3-dione (0.20 g, 0.55 mmol, from Example A2). The reaction was heated at reflux for 20 minutes, then cooled to 0° C. The resulting precipitate was removed by filtration, washed with cold acetonitrile, and dried to give 0.15 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 20 minutes
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with cold acetonitrile
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ae0d2dbd7d884c85838205bd650ebd24
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362181B1

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