反応 #1479438

反応方程式

dimethyl 2-(5-fluoro-2-nitrophenyl)malonate

hydrogen

→

5-fluoro-3-methoxycarbonyloxindole

収率 118.4%

溶媒

methanol

反応条件

後処理

1. 1
   その他In a flask made of glass
2. 2
   その他equipped with a stirrer
3. 3
   その他synthesized
4. 4
   その他a normal pressure, the mixture was reacted at the same temperature for 3 hours
5. 5
   その他After completion of the reaction
6. 6
   ろ過the reaction mixture was filtered
7. 7
   その他to remove the catalyst
8. 8
   濃縮the filtrate was concentrated under reduced pressure, and 80 ml of methanol and 240 ml of water
9. 9
   workup.ADDITIONwere added to the resulting
10. 10
    濃縮concentrate
11. 11
    温度cooled to 10° C
12. 12
    ろ過Then, after filtration of the precipitated crystals, they
13. 13
    その他were dried

実験手順

In a flask made of glass equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet tube and having an inner volume of 500 ml were charged 60.0 g (0.22 mol) of dimethyl 2-(5-fluoro-2-nitrophenyl)malonate synthesized according to Example 1 with a purity of 98% and 228 g of methanol under argon atmosphere. Under stirring, while maintaining the temperature of the mixture to 40 to 45° C., 3.0 g (0.72 mmol in terms of the palladium atom) of 5% by weight palladium/carbon (49% hydrated product) was added to the mixture. Then, while blowing hydrogen with a flow rate of 123 ml/min. and a normal pressure, the mixture was reacted at the same temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered to remove the catalyst, the filtrate was concentrated under reduced pressure, and 80 ml of methanol and 240 ml of water were added to the resulting concentrate and cooled to 10° C. Then, after filtration of the precipitated crystals, they were dried to obtain 54.5 g (isolation yield: 94%) of 5-fluoro-3-methoxycarbonyloxindole as white crude crystals with a purity of 80% (analytical value by high performance liquid chromatography).

出典