Sodium Hydroxide → HCID 178424052, compound

Participants

Reaction Steps

2-Nitro-3,4,6-trimethylaniline (10.2 g, 0.057 mol) was dissolved in 95% ethanol (900 ml) and hydrogenated in the presence of Pd/C-catalyst until the theoretical amount of hydrogen had been consumed (1 hour). The whole mixture was transferred to another flask and potassium ethylxanthate (12.8 g, 0.080 mol) dissolved in water (12.5 ml) was added. The mixture was refluxed overnight, 2M NaOH (20 ml) was added and the volatiles were evaporated off. The residue was dissolved in methanol (300 ml) and the catalyst was filtered off. Part of the solvent (200 ml) was evaporated off. Water (100 ml) was added and the mixture was acidified with acetic acid (10 ml) dissolved in water (20 ml). The crystalline precipitate was filtered off, washed with water and dried under reduced pressure, giving the desired product (7.2 g, 66%), NMR: δ (CDCl3) 2.0(s,3H), 2.05(s,3H), 2.1(s,3H), 3.3(br.s, 1H), 6.5(s,1H).

Provenance & Evidence