Hydrochloric Acid → 2-(1H-Pyrrol-1-yl)isoindoline-1,3-dione

HRID 1851081Notes

Reaction equation

HRID 1851081 reaction equation
[NH2:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1.Cl>O1CCOCC1>[C:3]1(=[O:12])[N:2]([N:1]2[CH:15]=[CH:19][CH:18]=[CH:17]2)[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74645N-AminophthalimideHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dioneYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-aminophthalimide (29.0 g, 178.8 mmol) and 2,5-dimethoxytetrahydrofuran (24.2 mL, 187.8 mmol) in anhydrous dioxane (290 mL) was stirred under reflux. While heating so that the resulting solution remained yellow, 5 N hydrochloric acid solution was cautiously added. The resulting mixture was allowed to cool to room temperature. The produced solid was filtered and washed with a 1:3 solution of dioxane and water. The target compound was yielded as a white solid (34.9 g, 164.5 mmol, 92% yield).

Workup

  1. temperatureunder reflux
  2. temperatureWhile heating so that the resulting solution
  3. filtrationThe produced solid was filtered
  4. washwashed with a 1:3 solution of dioxane and water

Sources & evidence

ORD record
ord-d73f6022f7314eedb8470d2e2e297b4a
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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