Sodium Sulfate → 6,7-Dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline methanol

HRID 463714Notes

Reaction equation

HRID 463714 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[C:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[N:8][CH:7]=1)=O)C.[H-].COCCO[Al+]OCCOC.[Na+].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:18][CH3:19])[C:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=[N:8][CH:7]=[C:6]2[CH2:4][OH:3]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 540263956,7-Dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinolinecarboxylic acid ethyl ester

Product 1

HCID 135605346,7-Dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline methanolYield 72.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 41.1 g of 6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinolinecarboxylic acid ethyl ester in 250 ml of dry tetrahydrofuran was chilled to 0° and treated dropwise over 30 minutes with 62.8 ml of 3.5M sodium bis-(2-methoxyethoxy)aluminum hydride in toluene solution. After stirring at 0° for three hours, 60 ml of saturated aqueous sodium sulfate solution was cautiously added and the mixture was stirred until granular. The supernatant solution was decanted, the residue was extracted with warm methylene chloride, and the combined organic solutions were evaporated in vacuo. The residue was dissolved in methylene chloride, washed with water, dried over sodium sulfate, and concentrated. Crystallization from methylene chloride/ethyl acetate provided 26.7 g of 6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]-4-isoquinoline methanol as a white solid, mp 140°-146°.

Workup

  1. stirringthe mixture was stirred until granular
  2. customThe supernatant solution was decanted
  3. extractionthe residue was extracted with warm methylene chloride
  4. customthe combined organic solutions were evaporated in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customCrystallization from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-4cbcc4e174fb48be8e4ca2a41709763d
Source dataset
uspto-grants-1985_10
Patent number
US04544657

Reaction notes

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