Hydrochloric Acid → 4-[2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]aniline

HRID 1192844Notes

Reaction equation

HRID 1192844 reaction equation
Cl.C(O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:11][CH2:10]2.[OH-].[Na+]>[Fe].O.ClCCl.C(Cl)(Cl)Cl.CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[CH2:13][N:12]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)[CH2:11][CH2:10]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 104274766,7-Dimethoxy-2-[2-(4-nitrophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 100412274-[2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl]anilineYield 90%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
80 °C

Procedure

Iron (1.27 kg, 23.48 mol), hydrochloric acid (127 mL, 1.54 mol) and 6.7 L of 50% aqueous ethanol were added to a reactor, and stirred for 1 hour at 80° C. 6,7-dimethoxy-2-(4-nitrophenethyl)-1,2,3,4-tetrahydroisoquinoline (1.3 kg, 3.91 mol) obtained in Step 1-1 was slowly added thereto for one hour, followed by stirring for 3 hours at 80° C. After checking completion of the reaction by thin layer chromatography (eluent: chloroform/methanol=15/1), the reaction mixture was cooled to room temperature. 5.3 L of dichloromethane and 5.3 L of water were added thereto, the reaction mixture was neutralized by adding 804 mL of 10% aqueous sodium hydroxide. The resulting mixture was filtered through a Celite pad and washed with 3 L of methylenechloride. The organic layer was collected, dried over magnesium sulfate, and then filtered. The solvent was removed under reduced pressure, and dried with hot air at 40° C. in an oven to obtain the title compound (1.05 kg, 90%).

Workup

  1. waitfor one hour
  2. stirringby stirring for 3 hours at 80° C
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationThe resulting mixture was filtered through a Celite pad
  5. washwashed with 3 L of methylenechloride
  6. customThe organic layer was collected
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customdried with hot air at 40° C. in an oven

Sources & evidence

ORD record
ord-c91960c4ba274f3996983cec5ccbe8db
Source dataset
uspto-grants-2014_03
Patent number
US08680277B2

Reaction notes

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