Methanol → 5,6-Dihydroxy-N-methylisoindoline hydrobromide

HRID 1032489Notes

Reaction equation

HRID 1032489 reaction equation
[Br-:1].[CH2:2]([N+:9]1(C)[CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[C:14]([OH:18])[CH:15]=2)[CH2:10]1)C1C=CC=CC=1.CO.[H][H]>[C].[Pd].C(O)(=O)C>[BrH:1].[OH:19][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][C:14]=1[OH:18])[CH2:17][N:9]([CH3:2])[CH2:10]2

Participants

6

Reactant 3

HCID 887MethanolHCID 14993734N-benzyl-5,6-dihydroxy-N-methylisoindolinium bromideHCID 178418361HCID 178418361, compound

Product 1

HCID 140984225,6-Dihydroxy-N-methylisoindoline hydrobromide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

1.0 g (2.97 mmol) of N-benzyl-5,6-dihydroxy-N-methylisoindolinium bromide obtained in Example 4 was dissolved in a solution comprising 10 ml of methanol and 10 ml of acetic acid, and 300 mg of a 10% palladium carbon catalyst was added thereto. Then, the catalytic reduction was conducted at 60° C. for 6 hours in a hydrogen gas stream. After filtering off the catalyst, the filtrate was evaporated to dryness under reduced pressure. To the residue, 10 ml of methanol was added, and the mixture was left to cool. The precipitated crystals were collected by filtration and washed with 10 ml of acetone to obtain 500 mg of the above identified compound as white crystals.

Workup

  1. additionwas added
  2. filtrationAfter filtering off the catalyst
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. additionTo the residue, 10 ml of methanol was added
  5. waitthe mixture was left
  6. temperatureto cool
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with 10 ml of acetone
  9. customto obtain 500 mg of the

Sources & evidence

ORD record
ord-1d3cb6fe86164c3e927cd40d5058adb7
Source dataset
uspto-grants-1990_09
Patent number
US04958029

Reaction notes

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