Preparation of 4-(3-nitrophenyl)pyridine

Details Preparation of 4-(3-nitrophenyl)pyridine Preparation of 4-(3-nitrophenyl)pyridine

1976-02-20

1977-02-15

Rotman, Alan L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260290R, 2602955R, 260287R, 260471R, C07D21326

Patent

active

040082393

ABSTRACT:
4-(3-Nitrophenylpyridine and intermediate useful in the preparation of 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinolinecarboxylates, which are useful as antibacterial agents, is prepared by reacting 3-nitrobenzaldehyde with two molar equivalents of di-(lower-alkyl) oxalacetate (II) in the presence of a catalytic condensing agent, preferably piperidine and/or its acetate, to produce tetra-(lower-alkyl) 3-(3-nitrophenyl)-1,5-pentanedione-1,2,4,5-tetracarboxylate (III), reacting III with ammonia to produce tetra-(lower-alkyl) 1,4-dihydro-4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (IV), oxidizing IV to produce tetra-(lower-alkyl) 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylate (V), hydrolyzing V to produce 4-(3-nitrophenyl)-2,3,5,6-pyridinetetracarboxylic acid (VI) and decarboxylating VI to produce 4-(3-nitrophenyl)pyridine (VI). Intermediates III, IV, V and VI are novel.

REFERENCES:
elderfield, Heterocyclic Compounds, vol. I, John Wiley & Sons Pub., pp. 574-577 (1950).
Klingsberg, Pyridine and Its Derivatives, Part Three, Interscience Pub. (1962).

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