O-Methyltyramine → 5,6,7,8-Tetrahydro-5-[[2-(4-methoxyphenyl)ethyl]amino]-1-methyl-2(1H)-quinolinone

A mixture of 2-(4-methoxyphenyl)ethylamine (5.6 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 39 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. The residue was washed with diethyl ether to afford 7.8 g (81%) of product. Recrystallization from ethyl acetate/hexanes provided the analytical sample, mp 97°-99° C.

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. washThe residue was washed with diethyl ether

ORD-Eintrag

ord-93adbae73078457caa96daf3e022cf96

Quelldatensatz

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05310914