Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1998-03-05
1999-06-29
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544393, 544395, 546232, 546233, 546234, 560 30, 560 31, C07D29514
Patent
active
059170379
ABSTRACT:
The present invention relates to a process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkylaminoanilines, which comprises reacting, in a first step, an orthonitrochlorobenzene of the formula (1) ##STR1## in which X is Cl or F, with a secondary amine of the formula (2) HNR.sup.1 R.sup.2, in which R.sub.1 and R.sup.2, independently of one another, are identical or different and are an alkyl radical having from 1 to 10 carbon atoms or, together with the N atom to which they are bonded, form a ring having from 3 to 7 members, in the presence of a base in the presence or absence of a solvent at from -10 to 120.degree. C., reacting, in a second step, the 2-chloro-4-dialkylamino-5-fluoronitrobenzene with hydrogen at from 30 to 150.degree. C. and from 1 to 100 bar in the presence of a base and a noble-metal catalyst and, in a third step, extracting the 3-fluoro-4-dialkylaminoaniline from the reaction mixture using an aqueous solution of an acid as a salt dissolved in water, removing the aqueous phase and reacting the 3-fluoro-4-dialkylaminoaniline salt, dissolved in water, with a chloroformate of the formula (3) ClCO.sub.2 R.sup.3, in which R.sup.3 is an alkyl radical having from 1 to 10 carbon atoms or an aralkyl radical having from 7 to 20 carbon atoms, at from 0 to 100.degree. C. in the presence of a basic compound.
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Rene Beugelmans et al. "Snythese d heterocycles a 5 et 6 chainons par une strategie combinant des reactions SNAr et SRN1" Bulletin de la Societe Chimique de France., Bd. 132, Nr. 3, 1995, Paris FR, Seiten 306-313, XP002070210.
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Papenfuhs Theodor
Schach Thomas
Clariant GmbH
Hanf Scott E.
Ramsuer Robert W.
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