The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jun. 29, 1999

Filed:

Mar. 05, 1998
Applicant:
Inventors:

Thomas Schach, Gernsheim, DE;

Theodor Papenfuhs, Frankfurt, DE;

Assignee:

Clariant GmbH, Frankfurt, DE;

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07D / ;
U.S. Cl.
CPC ...
544166 ; 544393 ; 544395 ; 546232 ; 546233 ; 546234 ; 560 30 ; 560 31 ;
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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