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Trifluoroacetic acid → HCID 13109064, compound

HRID 1462975
Notes
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Reaction equation

HRID 1462975 reaction equation
[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=2)[CH:5]1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>O=[V].Cl.Cl.Cl.C(Cl)Cl>[CH2:1]([N:4]1[CH:5]2[C:6]3=[C:7]([C:8]([OH:16])=[C:9]([O:14][CH3:15])[CH:10]=[C:11]3[CH2:12][CH2:13]1)[C:23]1[CH:22]=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=1[CH2:17]2)[CH:2]=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13109061HCID 13109061, compound

Product 1

HCID 13109064HCID 13109064, compound

Reagents, catalysts & solvents 2

HCID 24410Vanadium trichloride oxideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

22 g. (59.54 mmol) (+)-2-Allyl-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in a mixture of 190 ml. trifluoroacetic acid and 190 ml. anhydrous methylene chloride are mixed at -10° C., with the exclusion of moisture, with a solution of 6.0 ml. (11.04 g., 63.7 mmol) vanadium oxytrichloride in 190 ml. anhydrous methylene chloride. The reaction mixture is stirred for 30 minutes at -10° C., for 1 hour at 0° C. and for 2 hours at ambient temperature. Thereafter, the reaction mixture is concentrated to about one third of its volume by evaporation of the solvent in a vacuum at ambient temperature. The residue is mixed with ice water and extracted with chloroform. The chloroform phase is rendered basic with an aqueous solution of ammonia and worked up in the usual manner. By crystallisation from ethanol, there is obtained (+)-6-allyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenzo(de,g)quinoline; m.p. 85°-93° C./134°-138° C.

Workup

  1. concentrationThereafter, the reaction mixture is concentrated to about one third of its volume by evaporation of the solvent in a vacuum at ambient temperature
  2. additionThe residue is mixed with ice water
  3. extractionextracted with chloroform
  4. customBy crystallisation from ethanol

Sources & evidence

ORD record
ord-d32b274d02964fb980a0976183d621ff
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04461895

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes