Potassium Carbonate → 4-Methyl-1-phenyl-2(1H)-quinolone

HRID 1077685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077685
C=C1OC(=O)C1.[OH:7][C:8]1[CH:17]=[C:16]([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.C(=O)([O-])[O-].[K+].[K+].I[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>[Cu]>[CH3:18][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:8](=[O:7])[CH:17]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 12661DiketeneHCID 178429252HCID 178429252, Verbindung

Produkt 1

HCID 2691834-Methyl-1-phenyl-2(1H)-quinoloneAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

The starting 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) is prepared either by an Ullmann coupling according to a literature procedure (e.g. S. Wawzonek and T. V. Truong, J. HETEROCYCLIC CHEM., 25, 381 (1988).) or via the reaction of the corresponding diarylamine with diketene followed by acid cyclization (e.g. R. C. Elderfield, ed., HETEROCYCLIC COMPOUNDS vol. 4, pp. 1-331, 1952). Thus 10.0 g (62.9 mmoles) of 2-hydroxy-4-methylquinoline is heated at reflux with 24.0 g (377 mmoles) of copper powder, 8.68 g (62.9 mmoles) of potassium carbonate and 19.2 g (94 mmoles) of iodobenzene for 48 hours. The reaction is cooled to room temperature, partitioned between water and ethyl acetate, filtered, and the organic layer is dried over magnesium sulfate. The crude product is purified on a silica gel column, eluting with 1:1 ethyl acetate/hexanes to yield 8.1 g of the desired product.

Aufarbeitung

  1. customThe starting 1,2-dihydro-4-methyl-1-phenyl-2-quinolone (1) is prepared either by an Ullmann coupling
  2. custompartitioned between water and ethyl acetate
  3. filtrationfiltered
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. customThe crude product is purified on a silica gel column
  6. washeluting with 1:1 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6bb894781e8349a8a2147cc825da077d
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05545535

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