Réaction #46764

Équation de réaction

menthoyl chloride

4-Methoxy-2-nitroaniline

CH2Cl2

HCl

→

title compounds

Rendement 83.0%

2-Isopropyl-5-methyl-cyclohexanecarboxylic acid (4-methoxy-2-nitrophenyl)-amide

Rendement 83.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   AutreThe heterogeneous mixture was transferred to a separatory funnel
3. 3
   Autrewhere the aqueous phase was separated
4. 4
   Extractionre-extracted with CH2Cl2 (2×100 mL)
5. 5
   Lavagewashed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL)
6. 6
   Séchagedried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   AutreThe residue was purified by flash chromatography on silica gel (20 to 50% ethyl acetate/hexane for elution)

Mode opératoire

4-Methoxy-2-nitroaniline (5 g, 0.018 mol) was dissolved in pyridine (50) and treated with menthoyl chloride (3.57 g, 0.018 mol). The reaction mixture was heated to 50° C. and stirred vigorously for 6 h. The reaction mixture was cooled to room temperature and poured into a mixture of CH2Cl2 (100 mL) and 1N HCl (100 mL)). The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with CH2Cl2 (2×100 mL). The organic phases were combined and washed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (20 to 50% ethyl acetate/hexane for elution) provided the title compounds as colorless solid (4.9 g, 83%).

Source