反応 #2358595

反応方程式

NaOH

3-chloroaniline

NaNO2

SnCl2.2H2O

→

(3-chlorophenyl)hydrazine

収率 72.0%

溶媒

HCl

HCl

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise over a period of 3 h
2. 2
   温度while maintaining the temperature
3. 3
   workup.STIRRINGAfter stirring for a further 2 h at −5 to 0° C.
4. 4
   抽出extracted with EE (250 ml)
5. 5
   乾燥The combined organic phases were dried over magnesium sulphate
6. 6
   その他the solvent was removed under vacuum
7. 7
   その他The purification by column chromatography (SiO2, 8% EE/hexane)

実験手順

3-chloroaniline (K-IV) (1 eq., 50 g) was dissolved at −5 to 0° C. in concentrated HCl (300 ml) and stirred for 10 min. A mixture of NaNO2 (1.2 eq., 32.4 g), water (30 ml), SnCl2.2H2O (2.2 eq., 70.6 g) and concentrated HCl (100 ml) was added dropwise over a period of 3 h while maintaining the temperature. After stirring for a further 2 h at −5 to 0° C., the reaction mixture was set to pH 9 using NaOH solution and extracted with EE (250 ml). The combined organic phases were dried over magnesium sulphate and the solvent was removed under vacuum. The purification by column chromatography (SiO2, 8% EE/hexane) produced 40 g (72% yield) of (3-chlorophenyl)hydrazine (K-IV) as a brown oil.

出典