Aniline → 1-(hydroxymethyl)-4-(iminophenyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline

Reaktionsgleichung

[OH:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[C:6](=S)[O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3.O1CCOCC1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[OH:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[CH:6]([CH:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]2=[NH:28])[O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3

Komponenten

Edukt 3

HCID 6115Aniline

HCID 312751,4-Dioxane

HCID 148340121-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione

Produkt 1

HCID 867409521-(hydroxymethyl)-4-(iminophenyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinolineAusbeute 45 %

Versuchsvorschrift

To a solution of 3.09 g (0.01 mole) of 1-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione in 200 ml of dioxane 0.015 mole of HgO are added, and the mixture is reacted with 9.3 g (0.1 mole) of aniline. The reaction mixture is allowed to stand at room temperature for 24 hours, whereupon the HgS is filtered off, and the solvent and the excess of aniline are distilled off. The aimed compound is obtained in a yield of 45%.