3,4-Dichlorophenethylamine → HCID 10383281, compound

HRID 1033523Notes

Reaction equation

HRID 1033523 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[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:3]=[C:4]([CH2:9][CH2:10][NH:11][CH:18]2[CH2:19][CH2:20][CH2:21][C:22]3[N:13]([CH3:12])[C:14](=[O:24])[CH:15]=[CH:16][C:17]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 2179583,4-DichlorophenethylamineHCID 104422421-Methyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Product 1

HCID 10383281HCID 10383281, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(3,4-dichlorophenyl)ethylamine (3.8 g), 5,6,7,8-tetrahydro-1-methyl-5-oxo-2(1H)-quinolinone (3.0 g), and para-toluenesulfonic acid (130 mg) was heated in refluxing toluene (50 ml), with azeotropic removal of water, for 41 hrs. An additional 1 g of the amine and 0.1 g of para-toluenesulfonic acid were added, and the mixture was heated for an additional 24 hrs. The solution was cooled and the precipitate was collected. Sodium borohydride (0.6 g) was added to a solution of the precipitate in ethyl alcohol (50 ml), 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. The residue was dissolved in hot ethanol and treated with an equivalent amount of fumaric acid. The solid was collected and recrystallized from ethanol to provide 3.8 g (48%) of product, mp 172°-173° C.

Workup

  1. temperaturewas heated
  2. customwith azeotropic removal of water
  3. additionAn additional 1 g of the amine and 0.1 g of para-toluenesulfonic acid were added
  4. temperaturethe mixture was heated for an additional 24 hrs
  5. temperatureThe solution was cooled
  6. customthe precipitate was collected
  7. additionSodium borohydride (0.6 g) was added to a solution of the precipitate in ethyl alcohol (50 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 was concentrated
  15. dissolutionThe residue was dissolved in hot ethanol
  16. additiontreated with an equivalent amount of fumaric acid
  17. customThe solid was collected
  18. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-485914281d0945798dea240a11a23bc5
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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