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

HRID 1507889Notes

Reaction equation

HRID 1507889 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>[N:1]1([N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH:15]=[CH:19][CH:18]=[CH:17]1

Participants

5

Reactant 3

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

Product 1

HCID 8537192-(1H-Pyrrol-1-yl)isoindoline-1,3-dioneYield 53,205%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1,4-dioxane (50 mL) and N-aminophthalimide (5.0 g, 0.031 mmol) at rt was slowly added 2,5-dimethoxy tetrahydrofuran (15 g, 0.061 mmol). The resulting light yellow solution was heated to 100° C. for ˜16 h whereupon 5N HCl was carefully added at 100° C. giving a brown mixture. The mixture was allowed to cool room temperature, the solid thus separated was filtered and was rinsed with 1:3 of 1,4-dioxane in water. Drying afforded 3.5 g (54%) of the title compound as a white solid. LCMS (Condition D) m/z: 213 +ve.

Workup

  1. customat rt
  2. additionwas carefully added at 100° C.
  3. customgiving a brown mixture
  4. customthe solid thus separated
  5. filtrationwas filtered
  6. washwas rinsed with 1:3 of 1,4-dioxane in water
  7. customDrying

Sources & evidence

ORD record
ord-27ac6e97ea9441659ee32dc7e75508b8
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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