Urea → 3-Acetylpyridine
Reaction equation
NC(N)=O.[Br-:5].[C:6](C1C=CC=CN=1)(=[O:8])[CH3:7].[N:15]1[CH:20]=[CH:19][CH:18]=[CH2+:17][CH:16]=1>>[C:6]([C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)(=[O:8])[CH3:7].[Br:5][CH2:7][C:6]([C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)=[O:8]Participants
Reactant 1
Product 2
Procedure
Furthermore, it is known that 2,6-bis(2'-pyridyl)-pyridine is formed as a byproduct besides 2-(2'-pyridyl)-pyridine in the reaction of pyridine with potassium peroxydisulfate (East German Patent No. 23,118) or with pyridine-N-oxide in the presence of Pd-Pt-catalysts (Yakugaku Zasshi Vol. 93 (1973) pages 144-148). Also in the heating of pyridine in the presence of Raney nickel there is formed as byproduct 2,6-bis(2'-pyridyl)-pyridine and in the same manner there is formed in the heating of substituted pyridines the corresponding substituted compounds (J. Chem. Soc. (1956) pages 616-620). 2,6-Bis(3-pyridyl)-pyridine is produced when 3-acetyl pyridine is reacted with dimethylamine hydrochloride and formaldehyde to form an aminoketone and this aminoketone is further reacted with 3-pyridinium acetyl pyridine bromide obtained from 3-acetyl pyridine by way of 3-bromoacetyl pyridine (Synthesis (1976) pages 1-24).
Sources & evidence
- ORD record
- ord-189272b127834ae4a29c5518ed2ecc70
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171444
Reaction notes
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