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

HRID 364617Notes

Reaction equation

[I-].[OH:2][CH2:3][CH:4]1[CH:9]2[C:10]3[C:15]([CH2:16][CH2:17][N:8]2[CH2:7][O:6][CH:5]1SC)=[CH:14][C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3.C(O)C.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[OH:2][CH2:3][CH:4]1[CH:9]2[C:10]3[C:15]([CH2:16][CH2:17][N:8]2[CH:7]([CH:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[NH:27])[O:6][CH2:5]1)=[CH:14][C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3

Participants

Reactant 3

HCID 702Ethanol

HCID 6115Aniline

HCID 202393761-(hydroxymethyl)-2-(methylthio)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline iodide

Product 1

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

Procedure

To a solution of 4.51 g (0.01 mole) of 1-(hydroxymethyl)-2-(methylthio)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H-[1,3]oxazino[4,3-a]isoquinoline iodide in ethanol 9.3 g (0.10 mole) of aniline are added, and the reaction mixture is boiled for 3 hours. Upon cooling the product separates from the mixture in crystalline form.

Workup

temperatureUpon cooling the product

Sources & evidence

ORD record: ord-b87bcfcaf5e241aeb4a6cf6bd0cc02db
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605653

Reaction notes

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