反応 #162556

反応方程式

water

EtOAc

2-(1-bromoethyl)-3,5-dichloroquinoxaline

potassium phthalimide

→

2-(1-(3,5-dichloroquinoxalin-2-yl)ethyl)isoindoline-1,3-dione

収率 101.9%

溶媒

DMF

反応条件

後処理

1. 1
   その他The mixture was transferred to a 50 L separatory funnel
2. 2
   workup.STIRRINGwith stirring
3. 3
   ろ過was collected by filtration
4. 4
   その他phase was separated
5. 5
   抽出extracted again with EtOAc (2×4 L)
6. 6
   洗浄The combined organic layers were washed with brine
7. 7
   乾燥dried over anhydrous Na2SO4
8. 8
   ろ過filtered
9. 9
   その他the product was obtained as a white solid
10. 10
    ろ過The white solid was filtered
11. 11
    その他triturated with hexane
12. 12
    その他dried under vacuum

実験手順

To a solution of 2-(1-bromoethyl)-3,5-dichloroquinoxaline (1.00 Kg, 3.27 mol) in DMF (8.2 L) was added potassium phthalimide (1.21 Kg, 6.54 mol). The reaction mixture was stirred for 3 h. At this time LC-MS analysis showed that the reaction was complete. The mixture was transferred to a 50 L separatory funnel and water (12 L) and EtOAc (6 L) were added to it with stirring. A large amount of white solid crashed out and was collected by filtration. The aqueous. phase was separated and extracted again with EtOAc (2×4 L). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the volume was reduced to 5 L under reduced pressure. After cooling to rt, the product was obtained as a white solid. The white solid was filtered, triturated with hexane and dried under vacuum to give 2-(1-(3,5-dichloroquinoxalin-2-yl)ethyl)isoindoline-1,3-dione (1.24 Kg). 1H NMR (DMSO-d6) δ ppm 8.02-8.21 (2H, m), 7.83-8.02 (m, 5H), 5.89 (q, J=6.8 Hz, 1H), 1.87 (d, J=6.8 Hz, 3H). Mass Spectrum (ESI) m/z=372.0 (M+1).

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