Sulfuric Acid → HCID 14719560, compound

HRID 1768810Notes

Reaction equation

HRID 1768810 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:24])=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][NH:7][CH2:8][CH:9](O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:24])=[C:5]2[C:21]([CH:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=3)[CH2:8][NH:7][CH2:6]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 14719556HCID 14719556, compound

Product 1

HCID 14719560HCID 14719560, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

510 mg of α-[[(3-methoxy-2-methylbenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol was dissolved in 3.8 ml of trifluoroacetic acid, 0.12 ml of conc. sulfuric acid was added dropwise under ice cooling, and the mixture was allowed to react for 30 minutes. The reaction solution was concentrated, and subjected to azeotropic distillation with toluene 2 times. The residue was dissolved in chloroform, and basified by addition of 28% aqueous ammonia. The chloroform layter was collected, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 430 mg of 7-methoxy-4-(3,4-dimethoxyphenyl)-8-methyl-1,2,3,4-tetrahydroisoquinoline, m.p. 128°-129° C.

Workup

  1. customto react for 30 minutes
  2. concentrationThe reaction solution was concentrated
  3. distillationsubjected to azeotropic distillation with toluene 2 times
  4. dissolutionThe residue was dissolved in chloroform
  5. additionbasified by addition of 28% aqueous ammonia
  6. customThe chloroform layter was collected
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-125eda4305bf40528a40434c4092210d
Source dataset
uspto-grants-1995_01
Patent number
US05378849

Reaction notes

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