Réaction #992699

Équation de réaction

1,3-dimethyl-2-nitrobenzene

oxalyl chloride

3-methyl-2-nitrobenzeneacetic acid

→

title compound

3-methyl-N-(1-methylethyl)-2-nitrobenzeneacetamide

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreresulting in a solution
2. 2
   AutreThe volatiles were removed with a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 10 mL of dichloromethane
4. 4
   workup.ADDITIONHalf of this material was added dropwise at 0° C. to isopropylamine (1 mL) in 5 mL of dichloromethane
5. 5
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
6. 6
   workup.ADDITIONSaturated sodium bicarbonate solution was added
7. 7
   AutreThe solvent was removed with a rotary evaporator

Mode opératoire

To a slurry of 3-methyl-2-nitrobenzeneacetic acid (prepared by the method of H. Rapoport et al., J. Org. Chem., 1954, 77, 670-675 from 1,3-dimethyl-2-nitrobenzene, 0.70 g, 3.6 mmol) in 10 mL of dichloromethane was added oxalyl chloride (0.41 mL, 4.7 mmol) and two drops of N,N-dimethylformamide. The reaction mixture was stirred for 20 minutes, resulting in a solution. The volatiles were removed with a rotary evaporator. The residue was dissolved in 10 mL of dichloromethane. Half of this material was added dropwise at 0° C. to isopropylamine (1 mL) in 5 mL of dichloromethane. The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate solution was added, and the reaction mixture was passed through a Celite® diatomaceous filter aid cartridge. The solvent was removed with a rotary evaporator to afford the title compound as an orange solid (0.40 g).

Source