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Volumn 5, Issue 1, 2008, Pages 26-29

Copper(I) bromide promoted selective reduction of N-substituted phthalimides with zinc

Author keywords

Copper (I) bromide; Hydroxyphalimidines; Phthalimide; Reduction; Zinc

Indexed keywords


EID: 38949086596     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808783330171     Document Type: Article
Times cited : (3)

References (13)
  • 13
    • 38949090990 scopus 로고    scopus 로고
    • Typical procedure for the prepitration of hydroxyl lactam (3, A dry 100mL three-neck flask was charged with zinc dust (1.9g, 30mmol, the substrate (1, 10mmol) and 0.5mmol of copper (I) bromide in 20ml THF. The mbiwre was heated to reflux. After stirring for 4h at 60-70°C, the mixture was cooled to 0°C and added slowly to 3N hydrochloric acid to adjust PH to 3-5. The reaction continued at 0°C for 1-2h until the Phthalimide disappeared by TLC. The residue was diluted-with EtOAc, washed with aqueous sodium hydrogen carbonate and brine, and dried over MgSO4. The solvent was removed under reduced pressure, and the residue was purified by recrystallizing in ethanol to give the desired hydroxy-phalimidines as a white solid. 3-(1-hydroxy-3-oxoisoindolin-2-yl) propasenitrile (3j, Yiled: 830, IR(KBr, 3240cm-1, 2248.9cm-1, H NMR (300 MHz, DMSO, δ(ppm) 7.35-7.60 (m, 4H, 6.75 (d, J=8.7Hz, 1H) 5.94 (d, J=8.7Hz, 1H, 3.65-3.95 m, 1H
    • 13C NMR (75 MHz DMSO): 166.3, 144.8, 132.3, 131.1, 129.5, 123.7, 122.6, 119.1, 80.8, 35.0, 16.7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.