Potassium Carbonate → 4-Ethyl-2-methylpyridine
Reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=N[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[C:15]([CH3:16])=[N:14][CH2:13][CH2:12]N=1.[N+]([C:20]1[CH:21]=[C:22]([CH3:27])[N+:23]([O-:26])=[CH:24][CH:25]=1)([O-])=O.[C:28](=O)([O-])[O-:29].[K+].[K+]>>[CH2:9]([C:8]1[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=1)[CH3:10].[CH3:28][O:29][C:20]1[CH:21]=[C:22]([CH3:27])[N+:23]([O-:26])=[CH:24][CH:25]=1.[CH3:28][O:29][C:9]1[CH:12]=[CH:13][N:14]=[C:15]([CH3:16])[CH:10]=1Participants
Procedure
In the examples, certain of the starting materials were prepared in accordance with methods disclosed in the literature. For example, 2,3-dimethylpyrazine was prepared from 2,3-dimethyl-5,6-dihydropyrazine by the method of G. P. Rizzi, J. Org. Chem. 33, 1333 (1968) which itself was prepared by the procedure of T. Ishiguro and M. Matsumura, Yak. Zass. 78, 229 (1958). 4-Ethyl-2-methylpyridine was prepared by the procedure of Kaiser et al., J. Org. Chem. 38, 71 (1973). 4-Methoxy-2-picoline-N-oxide was prepared by reacting 4-nitro-2-picoline-N-oxide with methanolic potassium carbonate solution according to the general procedure of E. Profft et al., Germany (East) 69, 126; 10/5/69; Chem. Abs. 72, 90309w (1970). The crude product was not purified but was reacted directly with phosphorous trichloride in chloroform solution to give the known 4-methoxy-2-picoline starting material, based upon the general method of Herz and Tsai, J. Am. Chem. Soc. 76, 4184 (1954).
Workup
- custom33, 1333 (1968) which itself was prepared by the procedure of T
- customThe crude product was not purified
- customwas reacted directly with phosphorous trichloride in chloroform solution
Sources & evidence
- ORD record
- ord-fac269ef987e4cdea9a50d4deedd9982
- Source dataset
- uspto-grants-1987_07
- Patent number
- US04678501
Reaction notes
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