p-Toluenesulfonic acid → 2-Methyl-5-phenylquinoline

HRID 746258

反応式

HRID 746258 の反応式
O[C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([CH3:12])[CH:5]=[CH:4][C:3]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C(C)C)C=CC=CC=1>[Pd].Cl>[C:13]1([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 7406CumeneHCID 133457525-Hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine

生成物 1

HCID 224502702-Methyl-5-phenylquinoline

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒

実験手順

A mixture of 20 g (0.084 mole) of 5-hydroxy-5-phenyl-5,6,7,8-tetrahydroquinaldine, 10 g of 10% palladium on carbon, 2.3 g of para-toluenesulfonic acid and 200 ml of cumene was heated at its reflux temperature for 24 hours. The mixture was filtered hot, and then the filtrate was evaporated to provide a residue. This residue was dissolved in dilute hydrochloric acid. This solution was extracted with diethyl ether and the acid layer was then neutralized with 50% aqueous sodium hydroxide solution. The product was extracted into diethyl ether. The organic layer was dried and then evaporated to provide a solid residue. Recrystallization from methanol provided white crystals of 5-phenylquinaldine. Analysis: Calculated for C16H13N.H2O: %C, 81.0; %H, 6.4; %N, 5.8; Found: %C, 81.4; %H, 6.6; %N, 5.5. The structure assignment was confirmed by nuclear magnetic resonance spectral analysis.

後処理

  1. temperaturewas heated at its
  2. temperaturereflux temperature for 24 hours
  3. filtrationThe mixture was filtered hot
  4. customthe filtrate was evaporated
  5. customto provide a residue
  6. extractionThis solution was extracted with diethyl ether
  7. extractionThe product was extracted into diethyl ether
  8. customThe organic layer was dried
  9. customevaporated
  10. customto provide a solid residue
  11. customRecrystallization from methanol provided white crystals of 5-phenylquinaldine

出典と根拠

ORDレコード
ord-0fc275a1059540eb85407cb2dba41af9
出典データセット
uspto-grants-1986_07
特許番号
US04603199

関連ノート

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