Acetic Anhydride → HCID 178515264, Verbindung

HRID 1370325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370325
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]=[CH:13][CH:14]=[N:15]N(C)C)=[O:4].C(OC(=O)C)(=O)C.[O:28]=[C:29]1[CH:38]=[CH:37][C:36](=[O:39])[C:35]2[NH:34][C:33](=[O:40])[CH:32]=[CH:31][C:30]1=2>C(#N)C.[Pd]>[OH:40][C:33]1[CH:32]=[CH:31][C:30]2[C:29](=[O:28])[C:38]3[C:12]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[NH:5][C:3](=[O:4])[C:2]([F:1])([F:19])[F:20])=[CH:13][CH:14]=[N:15][C:37]=3[C:36](=[O:39])[C:35]=2[N:34]=1

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 2675922,5,8(1H)-QuinolinetrioneHCID 53710179HCID 53710179, Verbindung

Produkt 1

HCID 178515264HCID 178515264, VerbindungAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.9 g (6.5 mmol) of 4-(2-trifluoroacetamidophenyl)-1-dimethylamino-1-aza-1,3-butadiene, 2.2 mL of acetic anhydride and 1.6 g of Pd/C (10%) are successively added to a solution of 5,8-dioxocarbostyril (1.04 g, 5.9 mmol) in 500 mL of acetonitrile. The reaction medium is refluxed for 15 hours under nitrogen. After evaporating off the solvent on a rotary evaporator, the crude product obtained is purified by flash chromatography on silica (CH2Cl2 and then 95/5 CH2Cl2/MeOH) to give 400 mg of a yellow powder of compound CRL 8249 (or of its oxo tautomer in position 8).

Aufarbeitung

  1. temperatureThe reaction medium is refluxed for 15 hours under nitrogen
  2. customAfter evaporating off the solvent
  3. customon a rotary evaporator
  4. customthe crude product obtained
  5. customis purified by flash chromatography on silica (CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-bfd0d2f6a6734ddd9bca94843f4767e4
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583150B1

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