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

HRID 1195173Notes

Reaction equation

HRID 1195173 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][N:14]1[C:23]2[CH2:22][CH2:21][CH2:20][C:19](=O)[C:18]=2[CH:17]=[CH:16][C:15]1=[O:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:13][N:14]1[C:23]2[CH2:22][CH2:21][CH2:20][CH:19]([NH:12][CH2:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[C:18]=2[CH:17]=[CH:16][C:15]1=[O:25]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 951534-NitrophenethylamineHCID 104422421-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Product 1

HCID 184091025,6,7,8-Tetrahydro-1-methyl-5-[[2-(4-nitrophenyl)ethyl]amino]-2(1H)-quinolinoneYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-nitrophenyl)ethylamine (3.4 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 (70 ml), with azeotropic removal of water, for a total of 72 hrs. An additional 1.0 g of the amine was added at 24 and 48 hrs. The resulting solution was cooled and concentrated in vacuo. Sodium borohydride (0.6 g) was added to a solution of the residue in ethyl alcohol (70 ml). The resulting mixture was stirred at room temperature for 1 hr, and 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 concentrated. The residue was purified by high performance liquid chromatography (silica gel, eluted with methanol/ethyl acetate) to provide 3.8 g (69%) of product. Recrystallization from ethyl acetate afforded the analytical sample, mp 138°-139° C.,

Workup

  1. temperaturewas heated
  2. customwith azeotropic removal of water
  3. customfor a total of 72 hrs
  4. additionAn additional 1.0 g of the amine was added at 24 and 48 hrs
  5. temperatureThe resulting solution was cooled
  6. concentrationconcentrated in vacuo
  7. additionSodium borohydride (0.6 g) was added to a solution of the residue in ethyl alcohol (70 ml)
  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 concentrated
  15. customThe residue was purified by high performance liquid chromatography (silica gel, eluted with methanol/ethyl acetate)

Sources & evidence

ORD record
ord-f6986caafc0b4333a8e2abb6d39ffdd9
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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