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

HRID 1033522Notes

Reaction equation

HRID 1033522 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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 hr. 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.

Workup

  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

Sources & evidence

ORD record
ord-474346ee77b3431aa8f7acb128096e1f
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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