Acetic Anhydride → 5,6-Diacetoxy-2-acetylindoline

HRID 704461Notes

Reaction equation

HRID 704461 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][NH:7][CH2:6]2.C(O[C:17](=[O:19])[CH3:18])(=O)C>N1C=CC=CC=1>[C:3]([O:12][C:11]1[CH:10]=[C:9]2[C:8](=[CH:4][C:3]=1[O:2][C:11](=[O:12])[CH3:10])[NH:7][CH:6]([C:17](=[O:19])[CH3:18])[CH2:5]2)(=[O:2])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 200743492,3-dihydro-1H-isoindole-5,6-diol hydrobromide

Product 1

HCID 200743545,6-Diacetoxy-2-acetylindolineYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

500 mg (2.15 mmol) of 5,6-dihydroxyisoindoline hydrobromide was dissolved in 2.5 ml of pyridine, and 2.5 ml of acetic anhydride was added thereto at room temperature. The mixture was stirred at the same temperature for 30 minutes, and then excess pyridine and acetic anhydride were distilled off under reduced pressure. Ethyl acetate was added to the residue, and insoluble matters were filtered off. The filtrate was concentrated under reduced pressure, and the crystalline residue was washed with ethyl ether to obtain 532 mg (yield: 89.0%) of the above identified compound.

Workup

  1. customat room temperature
  2. distillationexcess pyridine and acetic anhydride were distilled off under reduced pressure
  3. additionEthyl acetate was added to the residue, and insoluble matters
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washthe crystalline residue was washed with ethyl ether
  7. customto obtain 532 mg (yield: 89.0%) of the

Sources & evidence

ORD record
ord-1ad1245ddf7144329cf86870edd6fbe9
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

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