HCID 14993733, compound → 5,6-Dimethoxy-2-methylisoindoline

HRID 1032488Notes

Reaction equation

HRID 1032488 reaction equation
[I-].[CH2:2]([N+:9]1(C)[CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:20][CH3:21])=[C:14]([O:18][CH3:19])[CH:15]=2)[CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[CH3:19][O:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:20][CH3:21])[CH2:10][N:9]([CH3:2])[CH2:17]2

Participants

5

Reactant 2

HCID 14993733HCID 14993733, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 190214005,6-Dimethoxy-2-methylisoindoline

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1.0 g (2.43 mmol) of N-benzyl-5,6-dimethoxy-N-methylisoindolinium iodide was dissolved in 40 ml of a 50% methanol aqueous solution, and 300 mg of a 10% palladium carbon catalyst was added. Then, the catalytic reduction was conducted at 50° C. for 6 hours in a hydrogen gas stream. After filtering off the catalyst, methanol was distilled off under reduced pressure, and the residual solution was adjusted to strongly alkaline by an addition of a 50% sodium hydroxide aqueous solution. Then, the solution was extracted twice with methylene chloride. The extract solution was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 200 mg of the above identified compound.

Workup

  1. additionwas added
  2. filtrationAfter filtering off the catalyst, methanol
  3. distillationwas distilled off under reduced pressure
  4. additionto strongly alkaline by an addition of a 50% sodium hydroxide aqueous solution
  5. extractionThen, the solution was extracted twice with methylene chloride
  6. dry with materialThe extract solution was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customto obtain 200 mg of the

Sources & evidence

ORD record
ord-93663239eea44b2b850f0c9f0d312007
Source dataset
uspto-grants-1990_09
Patent number
US04958029

Reaction notes

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