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

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

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

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

Sources & evidence

ORD record: ord-f283381da93346dab8a20399803753e3
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05004743

Linked notes

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