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

HRID 542193Notes

Reaction equation

HRID 542193 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][N:5]=1.[CH2:18]=[O:19]>CO>[OH:1][CH2:2][CH:3]([CH2:18][OH:19])[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][N:5]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 136966811-(beta-Hydroxyethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.01 mole of 1-(β-hydroxyethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 2 ml of a 37% aqueous formaldehyde solution are added, and the mixture is boiled in 30 ml of methanol for 2 hours. After evaporation the obtained oily residue is triturated with ether. Crystallization of the obtained product from a mixture of acetone and ether affords the desired compound, which has the same spectral characteristics as the product of Example 1. Melting point: 129° to 131 C.°

Workup

  1. customAfter evaporation the obtained oily residue
  2. customis triturated with ether
  3. customCrystallization of the obtained product
  4. additionfrom a mixture of acetone and ether

Sources & evidence

ORD record
ord-c54e270cedd441ccb6bab2db6e15bb90
Source dataset
uspto-grants-1987_04
Patent number
US04656179

Reaction notes

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