Acetaldehyde → 2-METHYL-4-NITRO-N,N-DIETHYLANILINE

Participants

Reaction Steps

3N Sulfuric acid (20 ml) was added dropwise to a stirred solution of 20% acetaldehyde (10 ml, 45.45 mmol) in THF (10 ml) at 0° C. After 15 min, this mixture was added to a solution of 2-methyl-4-nitro aniline (1 g, 6.6 mmol) in THF (10 ml). Sodium borohydride (1.5 g, 40.5 mmol) was added portion-wise and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was then diluted with water (60 ml), basified with sodium carbonate, and extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation to dryness gave a residue, which was chromatographed over silica gel using 0-3% ethyl acetate in pet ether to give diethyl-(2-methyl-4-nitro-phenyl)-amine (720 mg, 50%) as oil.

Provenance & Evidence