Preparation of 4-(3-nitrophenyl)pyridine

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

1974-02-25

1976-11-30

Moatz, Harry I.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260295AM, 260296R, 260290P, C07D21326

Patent

active

039949036

ABSTRACT:
4-(3-NITROPHENYL)PYRIDINE, AN INTERMEDIATE USEFUL IN THE PREPARATION OF THE ANTIBACTERIALLY ACTIVE 1-ALKYL-1,4-DIHYDRO-4-OXO-7-(4-PYRIDYL)-3-QUINOLINECARBOXYLIC ACIDS, IS PREPARED BY REACTING 4-(4-DIMETHYLAMINOPHENYL)PYRIDINE (I) with a demethylating agent to yield 4-(4-aminophenyl)pyridine (II), reacting said 4-aminophenyl compound (II) with a lower-alkanoylating agent to yield 4-[4-(lower-alkanoylamino)-phenyl]pyridine (III), nitrating the 4-(lower-alkanoylamino)-phenyl derivative (III) to yield 4-[4-(lower-alkanoylamino)-3-nitrophenyl]pyridine (IV), hydrolyzing the 4-(lower-alkanoylamino)-3-nitrophenyl compound (IV) to yield 4-(4-amino-3-nitrophenyl)-pyridine (V), and removing the 4-amino group of V by diazotization and reaction of the diazonium salt with a deaminating reducing agent to produce said intermediate 4-(3-nitrophenyl)pyridine (VI). Intermediates IV and V are novel.

REFERENCES:
zollinger, Azo & Diazo Chemistry Aliphatic and Aromatic Compounds, Title page & p. 168, (1961).
Cook et al., J. Chem. Society, (London), pp. 404-406, (1943).

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