p-Toluenesulfonic acid → 5-[[2-(2,4-Dichlorophenyl)ethyl]amino]-5,6,7,8-tetrahydro-1-methyl-2(1H)-quinolinone

HRID 1586999ノート

反応式

HRID 1586999 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH2:11].[CH3:12][N:13]1[C:22]2[CH2:21][CH2:20][CH2:19][C:18](=O)[C:17]=2[CH:16]=[CH:15][C:14]1=[O:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][CH:18]1[CH2:19][CH2:20][CH2:21][C:22]2[N:13]([CH3:12])[C:14](=[O:24])[CH:15]=[CH:16][C:17]1=2

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 1429382,4-DichlorophenethylamineHCID 104422421-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

生成物 1

HCID 184090995-[[2-(2,4-Dichlorophenyl)ethyl]amino]-5,6,7,8-tetrahydro-1-methyl-2(1H)-quinolinone収率 42%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2-(2,4-dichlorophenyl)ethylamine (3.8 g), 5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone (3.0 g), and para-toluenesulfonic acid (256 mg) was heated in refluxing toluene (50 ml), with azeotropic removal of water, for 40 hrs. An additional 2.0 g of the amine was added and the mixture was refluxed for 36 hrs. The solution was cooled and concentrated in vacuo. Sodium borohydride (0.6 g) was added to a solution of the residue in 50 ml of ethyl alcohol, and the mixture was stirred at room temperature for 1 hrs. The mixture was concentrated in vacuo, the residue was quenched with water, and the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Recrystallization of the residue from ethyl acetate/hexanes provided 2.5 g (42%) of product, mp 102°-103° C.

後処理

  1. temperaturewas heated
  2. customwith azeotropic removal of water
  3. additionAn additional 2.0 g of the amine was added
  4. temperaturethe mixture was refluxed for 36 hrs
  5. temperatureThe solution was cooled
  6. concentrationconcentrated in vacuo
  7. additionSodium borohydride (0.6 g) was added to a solution of the residue in 50 ml of ethyl alcohol
  8. concentrationThe mixture was concentrated in vacuo
  9. customthe residue was quenched with water
  10. extractionthe mixture was extracted with dichloromethane
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. concentrationthe filtrate was concentrated
  15. customRecrystallization of the residue from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-8f22ab64cd844ec3867ac06722f2d15c
出典データセット
uspto-grants-1993_06
特許番号
US05216164

反応ノート

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