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

HRID 1734408노트

반응식

HRID 1734408 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d86c8cdbb5b04449949d71e565624356
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534416

반응 노트

불러오는 중…