반응 #50462

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nitric acid

4-ethylisatin

→

5-nitro-4-ethylisatin

수율 52.0%

반응 조건

후처리

1. 1
   온도was cooled in an ice-water bath
2. 2
   기타A yellow solid precipitated immediately when this solution
3. 3
   workup.ADDITIONwas poured
4. 4
   기타over crushed ice

실험 절차

A beaker containing 15 mL of 90% fuming nitric acid was cooled in an ice-water bath. 2.1 g (12 mmoles) 4-ethylisatin was added in small portions over a five-minute period. The resultant red-orange solution was stirred while in the ice-water bath for 5 minutes, then warmed to room temperature and stirred for another 10 minutes. A yellow solid precipitated immediately when this solution was poured over crushed ice. 1.4 g (52% yield) 5-nitro-4-ethylisatin was obtained. NMR(CDCl3): 1.29(t,3H, J=7.5 Hz), 3.11(q,2H,J=7.5 Hz), 7.11 (d,1H,J=8.7 Hz), 8.27 (d,1H,J=8.7 Hz), 9.46(bs,1H). MS(m/z): 220(M+).

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