Trifluoroacetic acid → Trifluoroacetate

HRID 2295501Notes

Reaction equation

HRID 2295501 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][N:7]([CH3:14])[CH2:6][CH:5]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=1.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28]>O=[V].Cl.Cl.Cl.C(Cl)Cl>[OH:1][C:2]1[C:3]2=[C:4]3[CH:5]([CH2:15][C:16]4[CH:17]=[C:18]([OH:24])[C:19]([O:22][CH3:23])=[CH:20][C:21]=42)[CH2:6][N:7]([CH3:14])[CH2:8][C:9]3=[CH:10][C:11]=1[O:12][CH3:13].[F:25][C:26]([F:31])([F:30])[C:27]([O-:29])=[O:28]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20474672HCID 20474672, compound

Product 2

HCID 84468TrifluoroacetateHCID 12802082HCID 12802082, compound

Reagents, catalysts & solvents 2

HCID 24410Vanadium trichloride oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1 g. (3 mMol) (±)-6-Hydroxy-7-methoxy-4-(3-hydroxy-4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline is dissolved, with ice cooling, in 25 ml. trifluoroacetic acid and mixed at -10° C. with a solution of 0.42 ml. (0.77 g., 4.5 mMol) vanadium oxytrichloride in 5 ml. anhydrous methylene chloride within the course of 1 minute. The reaction mixture is allowed to react for 3 hours at -10° C., then concentrated in a vacuum to about one third of its volume and the concentrate partitioned between methylene chloride and water. Usual work up and crystallisation from acetone/diethyl ether gives (±)-5,6,6a,7-Tetrahydro-1,9-dihydroxy-2,10-dimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline in the form of its trifluoroacetate; m.p. 208°-215° C.; yield 60-70% of theory. Hydrochloride: m.p. >300° C. (decomp.), after recrystallisation from methanol/chloroform.

Workup

  1. customwithin the course of 1 minute
  2. customto react for 3 hours at -10° C.
  3. concentrationconcentrated in a vacuum to about one third of its volume
  4. customthe concentrate partitioned between methylene chloride and water
  5. customUsual work up and crystallisation from acetone/diethyl ether

Sources & evidence

ORD record
ord-db63ab5dc77442f28483abc03065b14b
Source dataset
uspto-grants-1984_01
Patent number
US04425350

Reaction notes

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