N-Aminophthalimide → 2-(1H-Pyrrol-1-yl)isoindoline-1,3-dione
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].C(O[CH:16]1[CH2:20][CH2:19][CH:18](OCC)O1)C>O1CCOCC1>[C:3]1(=[O:12])[N:2]([N:1]2[CH:16]=[CH:20][CH:19]=[CH:18]2)[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]12Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To 10.0 g(61.7 mmol) of N-aminophthalimide was added a solution of 12 ml(72.4 mmol) of 2,5-diethoxytetrahydrofuran in 100 ml of dioxane and 10 ml of 5 N hydrohloric acid was added thereto. The reaction mixture was stirred for 1 hour and cooled to 5° C. The resulting precipitate was filtered, recrystallized from dioxane:water(1:3), washed with ethanol and dried to give 10.3 g of 1-phthalimidopyrrole. This product was dissolved in 60 ml of methanol and 3 ml of 82% hydrazine hydrate was slowly added thereto. After refluxing the reaction mixture for 30 min, cooled to 0°~5° C. and 1.5 ml of glacial acetic acid was added thereto. The resulting precipitate was filtered off and the filtrate was concentrated under the reduced pressure to remove methanol. The concentrate was washed with diethyl ether and vacuum-distilled to give 2.4 g of the desired compound(47.3%).
Workup
- additionwas added
- filtrationThe resulting precipitate was filtered
- customrecrystallized from dioxane:water(1:3)
- washwashed with ethanol
- customdried
Sources & evidence
- ORD record
- ord-515bd4c7297245aa8b7138bf1b20f982
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05336673
Reaction notes
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