Hydrochloric Acid → 8-Chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1089485Notes

Reaction equation

HRID 1089485 reaction equation
C([N:8]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:15]2[C:10](=[C:11]([Cl:30])[C:12]([O:28][CH3:29])=[CH:13][CH:14]=2)[CH2:9]1)C1C=CC=CC=1.Cl>C(O)C>[Cl:30][C:11]1[C:12]([O:28][CH3:29])=[CH:13][CH:14]=[C:15]2[C:10]=1[CH2:9][NH:8][CH2:17][CH:16]2[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107884262-Benzyl-8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 106166778-Chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolineYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.13 g of 2-benzyl-8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline was dissolved in 28 ml of ethanol, and after adding thereto 0.22 ml of 12N hydrochloric acid, hydrogenation reaction was performed by addition of 0.1 g of 10%-paradium-carbon. After the hydrogenation reaction was over, the reaction solution was filetered, and concentrated. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 580 mg of 8-chloro-7-methoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline, m.p. 130°-132° C.

Workup

  1. additionafter adding
  2. customAfter the hydrogenation reaction
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5b3380b35ecc46caac1708711cdae616
Source dataset
uspto-grants-1990_10
Patent number
US04966904

Reaction notes

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