Potassium Carbonate → 4-Ethyl-2-methylpyridine

HRID 2118411

Reaktionsgleichung

Reaktionsgleichung von HRID 2118411
[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]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 222012,3-DimethylpyrazineHCID 852252,3-Dihydro-5,6-dimethylpyrazineHCID 95291Pyridine, 2-methyl-4-nitro-, 1-oxide

Produkt 3

HCID 683074-Ethyl-2-methylpyridineHCID 47377584-Methoxy-2-methylpyridineHCID 107018932-Methyl-4-methoxypyridine-N-oxide

Versuchsvorschrift

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).

Aufarbeitung

  1. custom33, 1333 (1968) which itself was prepared by the procedure of T
  2. customThe crude product was not purified
  3. customwas reacted directly with phosphorous trichloride in chloroform solution

Quellen und Nachweise

ORD-Eintrag
ord-fac269ef987e4cdea9a50d4deedd9982
Quelldatensatz
uspto-grants-1987_07
Patentnummer
US04678501

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