Formaldehyde → 1-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinoline

HRID 542192

Reaction equation

HRID 542192 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1.[CH2:16]=[O:17].[CH3:18][O-:19].[Na+]>CO>[OH:17][CH2:16][CH:1]([CH2:18][OH:19])[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4][N:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 226523,4-Dihydro-6,7-dimethoxy-1-methylisoquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 136966801-[Bis(hydroxymethyl)-methyl]-6,7-dimethoxy-3,4-dihydroisoquinolineYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1 mole (205.3 g) of 1-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline 100 ml of a 30% aqueous formaldehyde solution and then freshly prepared sodium methylate (1 g of sodium+50 ml of methanol) are added. The mixture is then slightly refluxed in 500 ml of methanol for 2 hours. The reaction mixture is evaporated under reduced pressure and the obtained crystalline product is recrystallized from a mixture of acetone and ether. The aimed compound is obtained with the same melting point as the product of Example 1.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customthe obtained crystalline product is recrystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-26e3d656308d441283e590390f0983fc
Source dataset
uspto-grants-1987_04
Patent number
US04656179

Linked notes

Loading…