Trifluoroacetic acid → HCID 70503637, compound

HRID 1462978Notes

Reaction equation

HRID 1462978 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:22][CH:23]=[C:24](C)[CH3:25])[CH:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)=[CH:4][C:3]=1[O:27][CH3:28].F[C:30](F)(F)C(O)=O>O=[V].Cl.Cl.Cl.C(Cl)Cl>[OH:1][C:2]1[C:11]2=[C:10]3[CH:9]([CH2:12][C:13]4[CH:14]=[C:15]([OH:21])[C:16]([O:19][CH3:20])=[CH:17][C:18]=42)[N:8]([CH2:22][C:23]([CH3:30])=[CH:24][CH3:25])[CH2:7][CH2:6][C:5]3=[CH:4][C:3]=1[O:27][CH3:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20452303HCID 20452303, compound

Product 1

HCID 70503637HCID 70503637, compound

Reagents, catalysts & solvents 2

HCID 24410Vanadium trichloride oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

6.49 g. (16.9 mmol) (-)-7-Hydroxy-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-(3-methylbut-2-enyl)-1,2,3,4-tetrahydroisoquinoline are then reacted in 55 ml. trifluoroacetic acid and 55 ml. anhydrous methylene chloride with 2.3 ml. (4.23 g., 24.4 mmol) vanadium oxytrichloride at -10° C. in a manner analogous to that described in Example 1. The (+)-5,6,6a,7-tetrahydro-1,9-dihydroxy-2,10-dimethoxy-6-(2-methylbut-2-enyl)-4H-dibenzo(de,g)quinoline obtained upon working up can, without further purification, be used in the subsequent methylation.

Workup

  1. customat -10° C.

Sources & evidence

ORD record
ord-62a43aec055f4d2786a7a0804fbb9832
Source dataset
uspto-grants-1984_07
Patent number
US04461895

Reaction notes

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