Hydrochloric Acid → Hydrochloric Acid

HRID 2295502Notes

Reaction equation

HRID 2295502 reaction equation
F[C:2](F)(F)C(O)=O.[OH:8][C:9]1[C:20]2=[C:21]3[CH:16]([CH2:17][C:18]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:19]=42)[CH2:15][N:14]([CH3:30])[CH2:13][C:12]3=[CH:11][C:10]=1[O:31][CH3:32].C1(C)C=CC=CC=1.[OH-].C1([N+](C)(C)C)C=CC=CC=1.[ClH:51]>C(Cl)(Cl)Cl.CN(C)C=O>[CH3:2][O:8][C:9]1[C:20]2=[C:21]3[CH:16]([CH2:17][C:18]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:19]=42)[CH2:15][N:14]([CH3:30])[CH2:13][C:12]3=[CH:11][C:10]=1[O:31][CH3:32].[ClH:51]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1140TolueneHCID 15913Trimethylphenylammonium hydroxideHCID 86739175(+/-)-5,6,6a,7-Tetrahydro-1-hydroxy-2,9,10-trimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline trifluoro acetate

Product 2

HCID 313Hydrochloric AcidHCID 12802084(+/-)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

2.2 g. (±)-5,6,6a,7-Tetrahydro-1-hydroxy-2,9,10-trimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline trifluoro acetate (see Example 3) are dissolved in 10 ml. of a mixture of toluene and dimethylformamide (9:1 v/v) and methylated with phenyltrimethylammonium hydroxide in a manner analogous to that described in Example 7. When the reaction is finished, the reaction mixture is evaporated in a vacuum and the residue is partitioned between water and methylene chloride. The organic phase is worked up in the usual manner and the crude product obtained is converted, either directly or after previous chromatography on silica gel with chloroform as eluent, into the hydrochloride by treatment with ethanolic hydrochloric acid. Crystallisation from ethanol/diethyl ether gives (±)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline in the form of a yellow hydrochloride; m.p. 212°-225° C.

Workup

  1. customthe reaction mixture is evaporated in a vacuum
  2. customthe residue is partitioned between water and methylene chloride
  3. customthe crude product obtained
  4. customCrystallisation from ethanol/diethyl ether

Sources & evidence

ORD record
ord-7cdeea92364b4a4190b2ab20c6dddae3
Source dataset
uspto-grants-1984_01
Patent number
US04425350

Reaction notes

Loading…