반응 #3232

반응 방정식

sodium nitrite

2-chloro-4-methyl-6-nitroaniline

sulfuric acid

→

title compound

수율 92.0%

3-Chloro-5-nitrotoluene

수율 92.0%

용매

water

ethanol

반응 조건

후처리

1. 1
   workup.ADDITIONto exceed 5° C. during the addition
2. 2
   workup.ADDITIONAfter the addition
3. 3
   온도at reflux until the evolution of gas from the reaction mixture
4. 4
   온도to cool
5. 5
   농축was concentrated
6. 6
   여과filtered
7. 7
   기타to remove the solids
8. 8
   농축The filtrate was concentrated
9. 9
   기타the residue chromatographed (eluant: diethyl ether/hexane; 1/9)

실험 절차

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).

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