2,6-Dimethylnitrobenzene → 3-methyl-N-(1-methylethyl)-2-nitrobenzeneacetamide

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).

1. customresulting in a solution
2. customThe volatiles were removed with a rotary evaporator
3. dissolutionThe residue was dissolved in 10 mL of dichloromethane
4. additionHalf of this material was added dropwise at 0° C. to isopropylamine (1 mL) in 5 mL of dichloromethane
5. stirringThe reaction mixture was stirred overnight at room temperature
6. additionSaturated sodium bicarbonate solution was added
7. customThe solvent was removed with a rotary evaporator

ORD-Eintrag

ord-6be066e91ff44d3aaf194c4243843944

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08012499B2