Réaction #3232

Équation de réaction

sodium nitrite

2-chloro-4-methyl-6-nitroaniline

sulfuric acid

→

title compound

Rendement 92.0%

3-Chloro-5-nitrotoluene

Rendement 92.0%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONto exceed 5° C. during the addition
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Températureat reflux until the evolution of gas from the reaction mixture
4. 4
   Températureto cool
5. 5
   Concentrationwas concentrated
6. 6
   Filtrationfiltered
7. 7
   Autreto remove the solids
8. 8
   ConcentrationThe filtrate was concentrated
9. 9
   Autrethe residue chromatographed (eluant: diethyl ether/hexane; 1/9)

Mode opératoire

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).

Source