Réaction #740886

Équation de réaction

methyl 3-valerylaminobenzoate

nitric acid

→

oil

Rendement 36.0%

Methyl 4-nitro-3-valerylaminobenzoate

Rendement 36.0%

Solvants

acetic anhydride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was stirred for two hours
3. 3
   Extractionwas extracted with ethyl acetate
4. 4
   LavageThe organic layer was washed with an aqueous solution of sodium bicarbonate and water
5. 5
   Autredried
6. 6
   AutreThe solvent was evaporated to dryness
7. 7
   Autrethe residue was purified by column chromatography on silica gel

Mode opératoire

To a solution of methyl 3-valerylaminobenzoate (2.3 g) in acetic anhydride (12 ml) was added dropwise fuming nitric acid (1.4 ml) while stirring under ice-cooling. To the mixture was added one drop of conc. sulfuric acid and the mixture was stirred for two hours. To the reaction mixture was added ice-water and it was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium bicarbonate and water and then dried. The solvent was evaporated to dryness, and the residue was purified by column chromatography on silica gel to afford a brown oil (1.0 g, 36%).

Source