Toluene → HCID 13109067, compound

HRID 1462972Notes

Reaction equation

HRID 1462972 reaction equation
[CH2:1]([N:4]1[CH:13]2[C:8]3=[C:9]([C:22]([OH:27])=[C:23]([O:25][CH3:26])[CH:24]=[C:7]3[CH2:6][CH2:5]1)[C:10]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:11]=1[CH2:12]2)[CH:2]=[CH2:3].[C:28]1(C)C=CC=CC=1.CN(C)C=O.[OH-].C1([N+](C)(C)C)C=CC=CC=1>CO>[CH2:1]([N:4]1[CH:13]2[C:8]3=[C:9]([C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=[C:7]3[CH2:6][CH2:5]1)[C:10]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[CH:14][C:11]=1[CH2:12]2)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 15913Trimethylphenylammonium hydroxideHCID 13109064HCID 13109064, compound

Product 1

HCID 13109067HCID 13109067, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.5 g. (12.2 mmol) (+)-6-Allyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline are reacted in 230 ml. of a mixture of toluene and dimethylformamide (9:1 v/v) with 20 ml. of a 1N solution of phenyltrimethylammonium hydroxide in methanol as described in Variant 1. After appropriate working up, there is obtained (+)-6-allyl-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-4H-dibenzo(de,g)quinoline, which is identical in every respect to the product obtained according to Variant 1. [α]DRT (hydrochloride): +117.7° (c=0.5, methanol).

Sources & evidence

ORD record
ord-b8789af47018480dad165886d7a4ae8d
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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