Sodium Hydroxide → HCID 19434249, compound

Participants

Reaction Steps

3-Amino-6-(3,4,5-trimethoxybenzyloxy)pyridazine (Intermediate 1, 2.91 g, 10 mMol) in acetic acid (20 ml) was treated dropwise with a solution of bromine (1.59 g, 10 mMol) in acetic acid (2 ml) over 5 minutes. After 0.5 hours, the mixture was filtered to give a cream solid which was suspended in water and basified with sodium hydroxide solution. The mixture was extracted with chloroform and the extracts were washed with water, dried (Na2SO4) and evaporated in vacuo to yield a cream solid which was recrystallised from toluene to give the title compound (2.76 g) as cream needles, m.p. 160°-161° C., NMR δH(CDCl3) 6.93(1H,s,ArH) 6.91(1H,JAB,8.8Hz,5H), 6.80(1H,JAB,8.8 Hz,4H), 5.49(2H,s,CH2), 4.95(2H, brs,NH2), 3.91(3H,s,OCH3), 3.90(3H,s,OCH3) and 3.89(3H,s,OCH 3).

Provenance & Evidence