Sodium Methoxide → HCID 20571808, compound

HRID 443817Notes

Reaction equation

HRID 443817 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][CH2:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 128748713-(Chloromethyl)isoquinoline hydrochloride

Product 1

HCID 20571808HCID 20571808, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3-chloromethylisoquinoline hydrochloride (96 g) and sodium methoxide (80 g) in methanol (1.5 liters) is heated under reflux for 8 hours. After cooling to 20° C., the mixture is filtered and the filtrate is evaporated to dryness at 50° C. under reduced pressure (20 mm Hg). The residue is taken up in methylene chloride (1 liter), the mixture is washed with water (3×150 cc), the organic phase is dried over magnesium sulphate and filtered, and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg). The oily residue is distilled at 82° C. under reduced pressure (0.6 mm Hg). 3-Methoxymethylisoquinoline (68 g), a colourless oil, is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 8 hours
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated to dryness at 50° C. under reduced pressure (20 mm Hg)
  5. washthe mixture is washed with water (3×150 cc)
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg)
  9. distillationThe oily residue is distilled at 82° C. under reduced pressure (0.6 mm Hg)

Sources & evidence

ORD record
ord-3f1045f71c36412cbee4600fb0a8b2de
Source dataset
uspto-grants-1981_04
Patent number
US04261992

Reaction notes

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