Benzaldehyde → 4-(2-phenylethenyl)pyridazine

Temperature

150 °C

Zinc chloride (820 mg, 6 mmol) was added to a stirred mixture of benzaldehyde (6.11 ml, 60 mmol) and 4-methylpyridazine (2.83 g, 30 mmol) and the resulting mixture heated for 20 hours at 150° C. The cool reaction mixture was partitioned between dichloromethane (40 ml) and 2M aqueous sodium hydroxide solution (20 ml), then the organic phase separated, combined with a dichloromethane extract (80 ml) of the aqueous phase, dried (Na2SO4) and evaporated under reduced pressure. The residual pale brown oil was purified by column chromatography on silica gel, using dichloromethane:methanol (99:1) as eluant, to give the title compound (3.65 g) as a pale brown solid. Found: C, 78.95; H, 5.52; N, 15.39. C12H10N2 requires C, 79.10; H, 5.53; N, 15.37%. δ (CDCl3): 6.96 (1H, d), 7.45 (5H, m), 7.55 (2H, m), 9.12 (1H, d), 9.30 (1H, s). LRMS: m/z 183 (M+1)+.

1. customThe cool reaction mixture
2. customwas partitioned between dichloromethane (40 ml) and 2M aqueous sodium hydroxide solution (20 ml)
3. customthe organic phase separated
4. extractionextract (80 ml) of the aqueous phase
5. dry with materialdried (Na2SO4)
6. customevaporated under reduced pressure
7. customThe residual pale brown oil was purified by column chromatography on silica gel

ORD record

ord-961f0e958368454ca524cad4fc8c6aec

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723719B1