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

HRID 1734408ノート

反応式

HRID 1734408 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 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. Wawzonek et al. 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.

後処理

  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

出典と根拠

ORDレコード
ord-d86c8cdbb5b04449949d71e565624356
出典データセット
uspto-grants-1996_07
特許番号
US05534416

反応ノート

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