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

HRID 2257484ノート

反応式

HRID 2257484 の反応式
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

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 12661DiketeneHCID 178429252HCID 178429252、化合物

生成物 1

HCID 2691834-Methyl-1-phenyl-2(1H)-quinolone収率 54.7%

試薬・触媒・溶媒 1

HCID 23978Copper触媒

実験手順

The synthetic precursor (1) is prepared either by an Ullmann coupling according to a literature procedure (Wawzonek, et al., J. HETEROCYCLIC CHEM., 25, 381 (1988)) or via the reaction of the corresponding diarylamine with diketene followed by acid cyclization (Elderfield, 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.

後処理

  1. customThe synthetic precursor (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

出典と根拠

ORDレコード
ord-3549a3e9ec0348d8b22b22d3785c192b
出典データセット
uspto-grants-1997_08
特許番号
US05658751

反応ノート

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