Dichloromethane → HCID 12802081, compound

HRID 2295500Notes

Reaction equation

HRID 2295500 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([N:5]1[CH2:14][CH:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:12]2[C:7](=[CH:8][C:9]([O:27][CH3:28])=[C:10]([OH:26])[CH:11]=2)[CH2:6]1)=[O:4].C(Cl)Cl.FC(F)(F)C(O)=O>O=[V].Cl.Cl.Cl.C(Cl)(Cl)Cl.CO>[F:30][C:2]([F:1])([F:29])[C:3]([N:5]1[CH2:6][C:7]2=[CH:8][C:9]([O:27][CH3:28])=[C:10]([OH:26])[C:11]3=[C:12]2[CH:13]([CH2:15][C:16]2[CH:17]=[C:18]([O:24][CH3:25])[C:19]([O:22][CH3:23])=[CH:20][C:21]=23)[CH2:14]1)=[O:4]

Participants

6

Reactant 3

HCID 6344Dichloromethane3×HCID 6422Trifluoroacetic acidHCID 20474671HCID 20474671, compound

Product 1

HCID 12802081HCID 12802081, compound

Reagents, catalysts & solvents 2

HCID 24410Vanadium trichloride oxideCatalyst2×HCID 21584188Chloroform methanolSolvent

Procedure

15.7 g. (36.9 mMol) (±)-N-Trifluoroacetyl-6-hydroxy-7-methoxy-4-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline are dissolved in 145 ml. dry methylene chloride and mixed with 145 ml. trifluoroacetic acid, while cooling with ice water and with the exclusion of moisture. A solution of 2.8 ml. (5.15 g., 29.73 mMol) vanadium oxytrichloride in 65 ml. anhydrous methylene chloride are added dropwise in the course of 10 minutes to this solution at -10° C., while stirring and in an inert gas atmosphere. After 30 minutes, a further addition of 2.8 ml. vanadium oxytrichloride in 65 ml. anhydrous methylene chloride takes place. The dark coloured reaction mixture is stirred for a further 10 minutes at -10° C. The TLC analysis (silica gel, chloroform/methanol 9:1 v/v) shows that the starting material is completely gone. The reaction mixture is concentrated in a vacuum in a rotary evaporator at ambient temperature to about one third of its original volume and the residue than partitioned between water and methylene chloride. After working up the extracts and crystallising the crude product from acetone, there is obtained (±)-5-trifluoroacetyl-5,6,6a,7-tetrahydro-1-hydroxy-2,9,10-trimethoxy-4H-dibenz(de,g)isoquinoline in practically quantitative yield; m.p. 210°-217° C.

Workup

  1. additiona further addition of 2.8 ml
  2. customreaction mixture
  3. stirringis stirred for a further 10 minutes at -10° C
  4. concentrationThe reaction mixture is concentrated in a vacuum in a rotary evaporator at ambient temperature to about one third of its original volume
  5. customthe residue than partitioned between water and methylene chloride
  6. customcrystallising the crude product from acetone

Sources & evidence

ORD record
ord-7313a8f775f5419b959b3cf62b0db57e
Source dataset
uspto-grants-1984_01
Patent number
US04425350

Reaction notes

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