Benzaldehyde → 3-(2-Phenylethenyl)pyridazine

HRID 990248

Reaction equation

HRID 990248 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1[N:11]=[N:12][CH:13]=[CH:14][CH:15]=1>[Cl-].[Zn+2].[Cl-]>[C:2]1([CH:1]=[CH:9][C:10]2[N:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 742083-Methylpyridazine

Product 1

HCID 2500313-(2-Phenylethenyl)pyridazineYield 59%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
150 °C

Procedure

Zinc chloride (820 mg, 6 mmol) was added to a stirred mixture of benzaldehyde (6.11 ml, 60 mmol) and 3-methylpyridazine (2.839, 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 residue was purified by column chromatography on silica gel, using dichloromethane: methanol (99:1) as eluant, to give the title compound (59%) as a solid. δ (CDCL3): 7.12 (1H, d), 7.34 (3H, m), 7.56 (2H, d), 7.72 (1H, d), 8.37 (1H, s), 8.50 (1H, s), 8.60 (1H, s), LRMS: m/z 183 (M+1)+.

Workup

  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 residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-68a68af14f8940a398e548916c46430f
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Linked notes

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