Pyridine → (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzoyl)-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline

HRID 597241Notes

Reaction equation

HRID 597241 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[NH:8][CH2:7][CH2:6]2.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38])[C:31](Cl)=[O:32].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])/[C:9](=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)/[N:8]([C:31](=[O:32])[C:30]1[CH:29]=[C:28]([O:27][CH3:26])[C:36]([O:37][CH3:38])=[C:35]([O:39][CH3:40])[CH:34]=1)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 681233913,4-Dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline

Product 1

HCID 68122585(Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzoyl)-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 6 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline and 6 parts of 3,4,5-trimethoxybenzoyl chloride in 50 parts of pyridine is heated at the boiling point under reflux in a nitrogen atmosphere for 45 minutes, whereupon 180 parts of chloroform is introduced. The resultant solution is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is taken up in benzene; and the benzene solution is chromatographed on silica gel, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvents. From an eluate comprising 30% ethyl acetate in benzene, on evaporation of solvent, (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzoyl)-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline melting at 195°-200° is obtained as the residue.

Workup

  1. temperatureis heated at the boiling point
  2. additionis introduced
  3. washThe resultant solution is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation
  6. customand the benzene solution is chromatographed on silica gel
  7. customFrom an eluate comprising 30% ethyl acetate in benzene, on evaporation of solvent

Sources & evidence

ORD record
ord-4dee3142ef264f08a5c8ffeb9b5591a5
Source dataset
uspto-grants-1977_03
Patent number
US04013666

Reaction notes

Loading…