Cinnamoylbenzene → 2,2':6',2''-Terpyridine
Reaction equation
C1(C=CC(C2C=CC=CC=2)=O)C=CC=CC=1.C(O[C:26]1[CH:41]=[CH:40][C:29]([CH:30]=[CH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=O)=[CH:28][CH:27]=1)CCCCCCC.[I-].[N:43]1C=CC=C[C:44]=1C(C[N+]1C=CC=CC=1)=O.[NH+:58]1C=CC=CC=1.[I-].C([O-])(=O)C.[NH4+]>C(O)(=O)C.CO>[CH:38]1[CH:37]=[CH:36][N:35]=[C:34]([C:32]2[CH:31]=[CH:30][CH:29]=[C:40]([C:41]3[CH:26]=[CH:27][CH:28]=[CH:44][N:43]=3)[N:58]=2)[CH:39]=1Participants
Procedure
The chalcone, 2-(4-octyloxycinnamoyl)pyridine (10.9 g) and the pyridinium salt N-(2-pyridylcarbonylmethyl)pyridinium iodide (10.8 g) were combined with 150 ml of methanol, 60 ml of glacial acetic acid and 60 g of ammonium acetate. The resulting mixture was refluxed under argon for 20 hours. After cooling, the precipitate formed was filtered, washed with methanol and recrystallized two times from acetonitrile to yield 7 g of pure terpyridine, mp 101°-102°. To 25 ml of cold oleum in a round bottom flask, 4 g of the pure terpyridine was added in small portions over about 30 minutes. The reaction mixture was allowed to come to room temperature and stirred overnight. The reaction mixture was poured onto ice, filtered; the resulting solid washed with cold water, then ethanol, and dried in vacuo to provide 3.22 g of product.
Workup
- temperatureThe resulting mixture was refluxed under argon for 20 hours
- temperatureAfter cooling
- customthe precipitate formed
- filtrationwas filtered
- washwashed with methanol
- customrecrystallized two times from acetonitrile
Sources & evidence
- ORD record
- ord-a6821404038348578fa0eb4ef95fd25d
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04568633
Reaction notes
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