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

HRID 364618Notes

Reaction equation

HRID 364618 reaction equation
[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

Participants

4

Reactant 3

HCID 6115AnilineHCID 312751,4-DioxaneHCID 148340121-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline-4-thione

Product 1

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

Procedure

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%.

Workup

  1. filtrationis filtered off
  2. distillationthe solvent and the excess of aniline are distilled off

Sources & evidence

ORD record
ord-f1700d0eeb994fb18ea79f6c3e24ee2c
Source dataset
uspto-grants-1986_08
Patent number
US04605653

Reaction notes

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