反応 #2439967

反応方程式

HCl

[2-Nitro-4-(4-nitrobenzoyl)phenyl] malonate

EtOH

→

6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one

収率 51.0%

溶媒

CHCl3

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度to reflux for 3 hours
3. 3
   ろ過filtered while hot and
4. 4
   その他The cooled reaction mixture
5. 5
   抽出extracted once with H2O (400 mL)
6. 6
   抽出extracted with a 95% EtOAc/5% i-prOH solution (3×400 mL)
7. 7
   乾燥dried over anhydrous Na2SO4
8. 8
   濃縮The solution was then concentrated in vacuo

実験手順

[2-Nitro-4-(4-nitrobenzoyl)phenyl] malonate (4.15 g, 9.61 mmol) was dissolved in EtOH (24 mL) after which Sn powder (9.16 g, 77 mmol) was added followed by dropwise addition of concentrated HCl(aq) (26 mL). The reaction mixture was allowed to reflux for 3 hours, filtered while hot and then allowed to cool to room temperature. The cooled reaction mixture was diluted with CHCl3 (400 mL) and then extracted once with H2O (400 mL). The aqueous layer was then neutralized with NaHCO3 (pH=7) and then extracted with a 95% EtOAc/5% i-prOH solution (3×400 mL). The organic layers were combined and dried over anhydrous Na2SO4. The solution was then concentrated in vacuo affording the 6-(4-Amino-benzoyl)-1,3-dihydro-indol-2-one in 51% yield (1.24 g, 4.90 mmol).

出典