7-Chloro-4-phenylquinoline → HCID 15512350、化合物

HRID 2422523ノート

反応式

HRID 2422523 の反応式
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][Mg+].[Br-]>CCOCC>[CH3:18][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 113454577-Chloro-4-phenylquinolineHCID 178418689HCID 178418689、化合物

生成物 1

HCID 15512350HCID 15512350、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 7-chloro-4-phenylquinoline (10.0 g, 41.7 mmol) and Ni(dppp)2Cl2 (2.26 g, 4.17 mmol) in ether (200 mL) was added dropwise 3.0 M MeMgBr (24.3 mL, 73 mmol) and heated at reflux for 3 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted with ether. The combined organic layer was washed with water and brine and then dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the resulting crude product was used in the next step without further purification. 1H NMR (400 MHz, acetone-d6): δ 8.9 (d, 1H), 7.93 (bs, 1H), 7.82 (d, 1H), 7.52-7.62 (m, 5H), 7.43 (dd, 1H), 7.35 (d, 1H), 2.60 (S, 3H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with ether
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting crude product was used in the next step without further purification

出典と根拠

ORDレコード
ord-66ed36310b09441990961ed03a297fbb
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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