Isophthalaldehyde → 3-(2-(6-Phenylpyridin-2-yl)ethenyl)benzaldehyde

HRID 1084425Notes

Reaction equation

HRID 1084425 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.[CH:14](=O)[C:15]1[CH:22]=[CH:21][CH:20]=[C:17]([CH:18]=[O:19])[CH:16]=1>[Cl-].[Zn+2].[Cl-]>[C:8]1([C:4]2[N:3]=[C:2]([CH:1]=[CH:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH:18]=[O:19])[CH:7]=[CH:6][CH:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 34777IsophthalaldehydeHCID 27628852-Methyl-6-phenylpyridine

Product 1

HCID 539539623-(2-(6-Phenylpyridin-2-yl)ethenyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
160 °C

Procedure

A mixture of 2-methyl-6-phenylpyridine (525 mg) (step 2), isophthalaldehyde (630 mg) and dry zinc chloride (40 mg) was heated at 160° C. under N2 for 3 hours. The resulting mixture was partitioned between 25% aqueous NH40Ac (20 cc) and ethyl acetate (20 cc) The organic layer was washed with H2O (10 cc), brine and solvent as removed in vacuo. The residue was purified by chromatography to afford the title compound.

Workup

  1. customThe resulting mixture was partitioned between 25% aqueous NH40Ac (20 cc) and ethyl acetate (20 cc) The organic layer
  2. washwas washed with H2O (10 cc), brine and solvent
  3. customas removed in vacuo
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-f283381da93346dab8a20399803753e3
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Reaction notes

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