Sulfuric Acid → HCID 15851832, compound

Participants

Reaction Steps

To a stirred suspension of 3,6-dichloropyridazine (22.5g, 0.151 mol), silver nitrate (12.7 g, 0.074 mol) and valeric acid (20.0 g, 0.195 mol ) in water (250 ml) was added a solution of sulfuric acid (49.3 g, 0.50 mol) in water (250 ml) at 50 deg. A solution of ammonium persulfate (93 g, 0.40 mol) in water (200 ml) was then added over 30 minutes at 60 deg. The resulting mixture was then stirred at 80 deg for 40 minutes and then cooled to room temperature. The mixture was adjusted to pH8 with 25% aqueous ammonium hydroxide and extracted with diethyl ether (3×250 ml). The combined ether extracts were washed with water (200 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography (5% ethyl acetate/hexane) to give 3,6-dichloro-4-n-butylpyridazine as a pale yellow oil (14.4 g, 47%). 1H-NMR (CDCl3) 7.30 (1H, s, 5-H), 2.65 (2H, t, Bu), 1.58 (2H, m, Bu), 1.37 (2H, m, Bu), 0.91 (3H, t, Bu).

Provenance & Evidence