Reacción #60310

Ecuación de reacción

4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester

aniline

water

→

pure desired product

Rendimiento 84.4%

4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester

Rendimiento 84.4%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is heated
2. 2
   Temperaturato reflux
3. 3
   Temperaturarefluxing
4. 4
   workup.WAITis continued for one hour
5. 5
   FiltraciónThe reaction mixture is filtered
6. 6
   Lavadowashed with 3:10 distilled water/MeOH (65 mL total)
7. 7
   workup.DISSOLUTIONThe solid is dissolved with CH2Cl2
8. 8
   Concentraciónconcentrated under reduced pressure

Procedimiento

4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid methyl ester 4a (2.20 g, 8.84 mmol) is suspended in MeOH (9.4 mL) and aniline (3.22 mL, 35.4 mmol) is added. The reaction mixture is heated to reflux with stirring under a nitrogen atmosphere. After 19 hours, the reaction is complete. Distilled water (3.22 mL) is added to the reaction mixture and refluxing is continued for one hour. The reaction mixture is cooled to 0° C. in an ice bath for 20 minutes. The reaction mixture is filtered and washed with 3:10 distilled water/MeOH (65 mL total) and then with MeOH. The solid is dissolved with CH2Cl2 and concentrated under reduced pressure to give 2.40 g (84%) of pure desired product. MS APCI (−) m/z 320.3 (M−1) detected.

Fuente