反応 #3232

反応方程式

sodium nitrite

2-chloro-4-methyl-6-nitroaniline

sulfuric acid

→

title compound

収率 92.0%

3-Chloro-5-nitrotoluene

収率 92.0%

溶媒

water

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONto exceed 5° C. during the addition
2. 2
   workup.ADDITIONAfter the addition
3. 3
   温度at reflux until the evolution of gas from the reaction mixture
4. 4
   温度to cool
5. 5
   濃縮was concentrated
6. 6
   ろ過filtered
7. 7
   その他to remove the solids
8. 8
   濃縮The filtrate was concentrated
9. 9
   その他the residue chromatographed (eluant: diethyl ether/hexane; 1/9)

実験手順

To a stirred mixture of 2-chloro-4-methyl-6-nitroaniline (7.39 g, 39.7 mM) and concentrated sulfuric acid (6.2 mL) in absolute ethanol (50 mL) at 0°-5° C. was slowly added a solution of sodium nitrite (6.85 g, 99.3 mM) in water (6 mL). The temperature of the reaction mixture was not allowed to exceed 5° C. during the addition. After the addition was completed, the reaction mixture was stirred at room temperature for 0.5 hr and then at reflux until the evolution of gas from the reaction mixture ceased. The reaction mixture was allowed to cool and was concentrated. The residue was slurried with ether and then filtered to remove the solids. The filtrate was concentrated and the residue chromatographed (eluant: diethyl ether/hexane; 1/9) to provide (6.25 g, 92%) the title compound as a yellow crystalline solid, mp 60.5-61° C.; MS(CI): 172 (M+H).

出典