Nitric Acid → HCID 70819396, compound

Participants

Reaction Conditions

Reaction Steps

Premixed nitric acid (d 1.5, 0.15 g) and sulfuric acid (0.05 g) was added dropwise at 5-10° C. to 4 (58 mg) in sulphuric acid (d 1.64, 0.5 g). The reaction mixture was heated at 80° C. for 1 hr then cooled and added to ice. Saturated aqueous sodium carbonate was added until effervescence ceased. The reaction mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue Elution with hexane/ethyl acetate gave 3-hexadecyl-2,6-dimethyl-5-nitropyridin-4(1H)-one (14) as a yellow oil: yield 41 mg (62%); silica gel TLC Rf 0.60 (1:1 hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 0.82-0.85 (m, 3H), 1.21-1.29 (m, 28H), 2.33 (s, 3H), 2.39 (s, 3H) and 2.46-2.52 (m, 2H).

Provenance & Evidence