تفاعل #3232

معادلة التفاعل

sodium nitrite

2-chloro-4-methyl-6-nitroaniline

sulfuric acid

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title compound

المردود 92.0%

3-Chloro-5-nitrotoluene

المردود 92.0%

المذيبات

water

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONto exceed 5° C. during the addition
2. 2
   workup.ADDITIONAfter the addition
3. 3
   درجة الحرارةat reflux until the evolution of gas from the reaction mixture
4. 4
   درجة الحرارةto cool
5. 5
   تركيزwas concentrated
6. 6
   ترشيحfiltered
7. 7
   أخرىto remove the solids
8. 8
   تركيزThe filtrate was concentrated
9. 9
   أخرىthe residue chromatographed (eluant: diethyl ether/hexane; 1/9)

الإجراء التجريبي

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).

المصدر