반응 #43545

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5-fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione

→

5-fluoro-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one

수율 90.3%

용매

water

hydrazine hydrate

ethanol

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후처리

1. 1
   추출extracted twice with ethyl acetate
2. 2
   건조The combined organics were dried over Na2SO4
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타The residue was purified by silica gel chromatography

실험 절차

A solution of 5-fluoro-1-(4-methoxy-benzyl)-1H-indole-2,3-dione (7.1 g, 24.9 mmol) in hydrazine hydrate (35 mL) and ethanol (15 mL) was refluxed overnight, diluted with water and extracted twice with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using a gradient of 0-100% ethyl acetate in hexane to afford 6.1 g (90%) of 5-fluoro-1-(4-methoxy-benzyl)-1,3-dihydro-indol-2-one; 1H NMR (CDCl3, 400 MHz) δ 3.59 (s, 2H), 3.77 (s, 3H), 4.83 (s, 2H), 6.63 (dd, 1H, J1=4.2, J2=8.6), 6.82-6.91 (m, 3H), 6.96-7.01 (m, 1H), 7.19-7.23 (m, 1H), 7.27-7.31 (m, 1H); HPLC-MS calcd. for C16H14FNO2 (M+H+) 272.1, found 272.3.

출처