p-Toluenesulfonic acid → 5-[2-(4-Chloro-phenyl)-ethylamino]-1-methyl-5,6,7,8-tetrahydro-1H-quinolin-2-one

HRID 1033520Notes

Reaction equation

HRID 1033520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[CH3:11][N:12]1[C:21]2[CH2:20][CH2:19][CH2:18][C:17](=O)[C:16]=2[CH:15]=[CH:14][C:13]1=[O:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH:17]2[CH2:18][CH2:19][CH2:20][C:21]3[N:12]([CH3:11])[C:13](=[O:23])[CH:14]=[CH:15][C:16]2=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 674302-(4-Chlorophenyl)ethylamineHCID 104422421-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Product 1

HCID 103584245-[2-(4-Chloro-phenyl)-ethylamino]-1-methyl-5,6,7,8-tetrahydro-1H-quinolin-2-oneYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-chlorophenyl)ethylamine (5.8 g), 5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone (5.5 g), and a catalytic amount of para-toluenesulfonic acid was heated in refluxing toluene (90 ml), with azeotropic removal of water, for 40 hrs. The solution was cooled and concentrated in vacuo. Sodium borohydride (1.1 g) was added to a solution of the residue in ethyl alcohol (90 ml), and the mixture was stirred at room temperature for 2 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 6.55 g (67%) of product, mp 110°-112° C.

Workup

  1. customwith azeotropic removal of water
  2. temperatureThe solution was cooled
  3. concentrationconcentrated in vacuo
  4. additionSodium borohydride (1.1 g) was added to a solution of the residue in ethyl alcohol (90 ml)
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe residue was quenched with water
  7. extractionthe mixture was extracted with dichloromethane
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated
  12. customRecrystallization of the residue from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d8da3132018b450d98592ee8438d1df3
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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