Hydrochloric Acid → 1-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methylisoquinolin-3(2H)-one--hydrogen chloride (1/1)

HRID 616707Notes

Reaction equation

HRID 616707 reaction equation
O1CCCC1.CN.[ClH:8].[CH3:9][O:10][C:11]1[C:20]([O:21][CH3:22])=[CH:19][C:18]2[C:13](=[CH:14][C:15](=[O:35])[N:16]([CH3:34])[C:17]=2[CH2:23][C:24]2[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=2)[CH:12]=1>CO>[ClH:8].[CH3:9][O:10][C:11]1[C:20]([O:21][CH3:22])=[CH:19][C:18]2[C:13](=[CH:14][C:15](=[O:35])[N:16]([CH3:34])[C:17]=2[CH2:23][C:24]2[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[C:26]([O:27][CH3:28])[CH:25]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 37731HCID 37731, compound

Product 1

HCID 241981361-[(3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methylisoquinolin-3(2H)-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The lactone (3.6 g., 0.01 mole) is suspended in 100 ml. of dry tetrahydrofuran and gaseous methylamine is passed therein until complete solution is obtained. The mixture is left standing overnight at room temperature and concentrated under reduced pressure to provide a residual oil which is taken up in methanol and acidified with 5N ethanolic hydrogen chloride. The acidified solution is cooled and the precipitated solid is collected and cyrstallized from methanol-ethyl acetate to provide 3.1 g. (76.5%) of 6,7-dimethoxy-2-methyl-1-veratryl-3(2H)-isoquinolone, m.p. 233°-236° C. (dec.) (uncorr.).

Workup

  1. customuntil complete solution is obtained
  2. waitThe mixture is left
  3. concentrationconcentrated under reduced pressure
  4. customto provide a residual oil which
  5. temperatureThe acidified solution is cooled
  6. customthe precipitated solid is collected
  7. customto provide 3.1 g

Sources & evidence

ORD record
ord-bde0ad879b8d4409bde06dbcca867d5e
Source dataset
uspto-grants-1978_02
Patent number
US04075344

Reaction notes

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