Toluene → (+/-)-5,6,6a,7-tetrahydro-2,3-dimethoxy-9,10-methylenedioxy-5-methyl-4H-dibenz(de,g)isoquinoline
Reaction equation
F[C:2](F)(F)C(O)=O.[OH:8][C:9]1[C:10]([O:30][CH3:31])=[CH:11][C:12]2[C:21]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:20]=3[CH2:19][CH:18]3[C:13]=2[C:14]=1[CH2:15][N:16]([CH3:29])[CH2:17]3.C1(C)C=CC=CC=1.[OH-].C1([N+](C)(C)C)C=CC=CC=1>CN(C)C=O>[CH3:31][O:30][C:10]1[C:9]([O:8][CH3:2])=[C:14]2[CH2:15][N:16]([CH3:29])[CH2:17][CH:18]3[CH2:19][C:20]4[CH:25]=[C:24]5[O:26][CH2:27][O:28][C:23]5=[CH:22][C:21]=4[C:12](=[C:13]23)[CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
10.65 g. (±)-5,6,6a,7-tetrahydro-3-hydroxy-2-methoxy-9,10-methylenedioxy-5-methyl-4H-dibenz(de,g)isoquinoline trifluoroacetate (see Example 1) are dissolved in 500 ml. of a mixture of toluene and dimethyl formamide (9:1) in a manner analogous to that described in Example 7 and methylated with phenyltrimethyl ammonium hydroxide. When the methylation is finished (monitoring with TLC), the reaction mixture is evaporated in a vacuum. After partitioning the residue between water and methylene chloride, working up the organic phase and crystallising from methanol/chloroform, there is obtained (±)-5,6,6a,7-tetrahydro-2,3-dimethoxy-9,10-methylenedioxy-5-methyl-4H-dibenz(de,g)isoquinoline in the form of cream-coloured crystals; m.p. 169°-172° C.
Workup
- customthe reaction mixture is evaporated in a vacuum
- customAfter partitioning the residue between water and methylene chloride
- customcrystallising from methanol/chloroform
Sources & evidence
- ORD record
- ord-e406470556ab4c90be93335e7f1a1f64
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04425350
Reaction notes
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