Hydrochloric Acid → N-(4-aminophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

HRID 35227Notes

Reaction equation

HRID 35227 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]2[CH3:27])=[O:12])=[CH:6][CH:5]=1)([O-])=O.C(OC(=O)C)C.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=3)[CH:14]2[CH3:27])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14230283N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

Product 1

HCID 21295812N-(4-aminophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinolineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-nitrophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (38.3 g, 0.1035 m) in a mixture of methanol (500 ml), ethylacetate (500 ml) and conc HCl (8 ml) in a pressure bottle was treated with 5.0 g 5% Pd/C catalyst under nitrogen and the mixture hydrogenated on a Parr apparatus at 50 psi for 4 hr. The catalyst was removed by filtration and the solvent evaporated to a solid residue. The solid was dissolved in water (2 liters), filtered, then basified to pH with 50% NaOH. Extraction with CHCl3 (3×250 ml) and evaporation of the extracts gave N-(4-aminophenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as an off-white solid, 30.4 g (86% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated to a solid residue
  3. dissolutionThe solid was dissolved in water (2 liters)
  4. filtrationfiltered
  5. extractionExtraction
  6. customwith CHCl3 (3×250 ml) and evaporation of the extracts

Sources & evidence

ORD record
ord-5b670290e9d74cae9410663458cdb8fc
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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