6,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline hydrochloride → 6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 35223

Reaction equation

HRID 35223 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:10]([CH3:16])=[N:9][CH2:8][CH2:7]2>CO.[Pd]>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[CH:10]([CH3:16])[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 1

HCID 123273036,7-Dimethoxy-1-methyl-3,4-dihydroisoquinoline hydrochloride

Product 1

HCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline hydrochloride (58.4 g, 0.24 m) in 1 liter of methanol and 5% Pd/C (5 g) were combined under nitrogen in a pressure bottle and the mixture hydrogenated at 40 psi and ambient temperature on a Parr apparatus for 18 hr. The catalyst was removed by filtration and the solvent evaporated. The residue was dissolved in H2O (1 liter), basified to pH 11 with 50% NaOH and extracted with CHCl3 (3×300 ml). The extracts were dried over MgSO4 and evaporated to dryness (aspirator, then high vacuum) to give 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline, 35.2 g (70% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in H2O (1 liter)
  4. extractionextracted with CHCl3 (3×300 ml)
  5. dry with materialThe extracts were dried over MgSO4
  6. customevaporated to dryness (aspirator

Sources & evidence

ORD record
ord-ac8f811fc9be49ed9ee94149cbb94b0a
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Linked notes

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