N-[2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethyl]benzamide → 3,4-Dihydro-6,7-dimethoxy-1-phenyl-3-(3-pyridyl)isoquinoline

HRID 464317Notes

Reaction equation

HRID 464317 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:19][C:20](=O)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>P(Cl)(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[N:19][CH:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:11]2

Participants

3

Reactant 1

HCID 13319894N-[2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethyl]benzamide

Product 1

HCID 133198953,4-Dihydro-6,7-dimethoxy-1-phenyl-3-(3-pyridyl)isoquinolineYield 93.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1.8 g of N-[2-(3,4-dimethoxyphenyl)-1-(3-pyridyl)ethyl]benzamide in 20 ml of phosphorus oxychloride are stirred at 60° C. for 5 hours and at 120° C. for 1.5 hours. The yellow precipitate is filtered off with suction, dissolved in 200 ml of water, and the solution is made alkaline with potassium carbonate and extracted twice with methylene chloride. 1.6 g of dihydroisoquinoline compound of melting point 180°-182° C. are isolated.

Workup

  1. filtrationThe yellow precipitate is filtered off with suction
  2. dissolutiondissolved in 200 ml of water
  3. extractionextracted twice with methylene chloride

Sources & evidence

ORD record
ord-57df71bd4f8f4d54b0aca8c2d3e9d4c5
Source dataset
uspto-grants-1985_10
Patent number
US04547508

Reaction notes

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