Process for preparing nitroaniline derivatives

Details Process for preparing nitroaniline derivatives Process for preparing nitroaniline derivatives

1994-07-11

1995-11-14

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564399, 564406, 564407, 564440, 564441, 564467, C07C20902

Patent

active

054668719

ABSTRACT:
A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.

REFERENCES:
patent: 5120853 (1992-06-01), Yoneyoshi et al.
Houben Weyl "Methoden der organischen . . . 4th ed., vol. XI/1 Stickstoffverbindungen" 1957, pp. 17-19.
Chem. Abs., vol. 77, No. 9, 1972, Aug. 28, Ohio, S. Yamada et al., "Alfa-Amination". . . p. 537, col 1.
Tetrahedron Letters, No. 51, 1965, Oxford F. Minisci et al. "Homolytic amination of aromatic". . . , pp. 4663-4667.
J. Am. Chem. Soc. 1992, 114, pp. 9237-9238 "Direct Coupling of Aniline and Nitrobenzene: . . . ".
J. Org. Chem. 1993, 58, pp. 6883-6888 "Amination of Nitrobenzene via Nucleophilic Aromatic Substitution for Hydrogen: . . . ".
J. Org. Chem. 1986, 51, pp. 5039-5040 "Direct Amination of Nitrobenzenes by Vicarious Nucleophilic Substitution".
J. Org. Chem. 1988, 53, pp. 3978-3982 "Alkylaminonitrobenzenes by Vicarious Nucleophilic Amination with 4-(Alkylamino)-1,2,4-triazoles".
J. Org. Chem. 1992, 57, pp. 4784-4785, "Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen".
Price, C. C. et al. Organic Synthesis, Collective Vol. III pp. 664-665 (1955).

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