Process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkyl

Details Process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkyl Process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkyl

1998-03-05

1999-06-29

Geist, Gary

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

Organic compounds

Chalcogen in the nitrogen containing substituent

544358, 546190, 560 22, C07D26530

Patent

active

059170360

ABSTRACT:
A process for the preparation of N-carboxyalkyl-3-fluoro-4-dialkylaminoanilines, which comprises reacting, in a first step, 2-chloro-4,5-difluoronitrobenzene of the formula (I) ##STR1## with a secondary amine of the formula (II) HNR.sup.1 R.sup.2, in which R.sup.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 5 to 7 members, in the presence of a water-soluble amine which forms hydrofluorides and hydrochlorides which are liquid at the reaction temperature and work-up temperature or soluble in the reaction mixture, in the presence or absence of a solvent at -10 to 120.degree. C., reducing, in a second step, the reaction mixture containing the 2-chloro-4-dialkylamino-5-fluoronitrobenzene using hydrogen at from 30 to 150.degree. C. and from 1 to 350 bar in the presence of the water-soluble amine and in the presence of a noble-metal catalyst and, in a third step, reacting the reaction mixture containing the 3-fluoro-4-dialkylaminoaniline with a chloroformate of the formula (IV) 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 the water-soluble amine.

REFERENCES:
patent: 3515744 (1970-06-01), Steinbrunn
patent: 3852332 (1974-12-01), Cross

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