Sulfuric Acid → HCID 14719560, compound

HRID 1590830Notes

Reaction equation

HRID 1590830 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 layer 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 layer 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-624ea2a4880447009610adf58fe58c28
Source dataset
uspto-grants-1993_04
Patent number
US05204468

Reaction notes

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