5,6,6a,7-tetrahydro-6-methyl-4H-Dibenzo(de,g)quinoline → HCID 21447042, compound

HRID 597388Notes

Reaction equation

HRID 597388 reaction equation
[BrH:1].N[C:3]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:4]=1[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][C:12]([O:17][CH3:18])=[C:13]([OH:16])[CH:14]=2)[CH2:9][CH2:8][N:7]1[CH3:19].C1C2=C3C(CC4C2=CC=CC=4)N(C)CCC3=CC=1>C(OCC)(=O)C.Br>[BrH:1].[OH:16][C:13]1[C:14]2=[C:15]3[CH:6]([CH2:5][C:4]4[C:3]2=[CH:23][C:22]([O:24][CH3:25])=[CH:21][CH:20]=4)[N:7]([CH3:19])[CH2:8][CH2:9][C:10]3=[CH:11][C:12]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 1149115,6,6a,7-tetrahydro-6-methyl-4H-Dibenzo(de,g)quinolineHCID 21447048HCID 21447048, compound

Product 1

HCID 21447042HCID 21447042, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The diazotization and cyclization of 1-(2'-amino-4'-methoxybenzyl)-2-methyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (4f) was carried out as in Example XVIII, except that the only residue containing the crude aporphine was quickly passed through a short column of silica gel (10 g, backed in chloroform) and eluted with 5% methanol-chloroform. Evaporation of the organic solvents gave a residue which was dissolved in ethyl acetate and heated with a few drops of 48% hydrogen bromide to give 1-hydroxy-2,10-dimethoxyaporphine hydrobromide (5f) in 47% yield, mp 219-221.

Workup

  1. washeluted with 5% methanol-chloroform
  2. customEvaporation of the organic solvents
  3. customgave a residue which

Sources & evidence

ORD record
ord-27f640513a564615802a5ae592907554
Source dataset
uspto-grants-1977_03
Patent number
US04013664

Reaction notes

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