Process for the preparation of N-alkylhalogenoanilines
AssigneeHoechst Aktiengesellschaft
InventorsWerner Brodt, Theodor Papenfuhs
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AssigneeHoechst Aktiengesellschaft
InventorsWerner Brodt, Theodor Papenfuhs
Estimating the term…
A process for the preparation of N-alkylhalogenoanilines of the formula (I) 100.degree. ##STR1## in which X is a chlorine or bromine atom and n is the number 1 or 2, R.sup.1 is an alkyl (C.sub.1 -C.sub.4) radical, R.sup.2 an alkyl (C.sub.1 -C.sub.6) radical or R.sup.1 and R.sup.2 together with the carbon atom can form a five- or six-membered cycloalkane ring, by reacting a halogenonitrobenzene of the formula (II) ##STR2## in which X and n have the abovementioned meanings with an at least stoichiometric amount of a carbonyl compound of the formula (III) ##STR3## in which R.sup.1 and R.sup.2 have the meanings mentioned or R.sup.1 and R.sup.2 together with the carbon atom of the carbonyl group can form a five- or six-membered cycloalkane ring, in an inert organic solvent at temperatures of about 10 to about 100.degree. C., at a hydrogen superatmospheric pressure of about 0 to about 50 bar, in the presence of a platinum catalyst on activated carbon.
A process for the preparation of N-alkylhalogenoanilines of the general formula (I) ##STR7## in which X is a chlorine or bromine atom and n is the number 1 or 2, R.sup.1 is a linear or branched alkyl (C.sub.1 -C.sub.4) radical, R.sup.2 a linear or branched alkyl (C.sub.1 -C.sub.6) radical or R.sup.1 and R.sup.2 together with the carbon atom to which they are bound can form a five- or six-membered cycloalkane ring, which comprises reacting a halogenonitrobenzene of the general formula (II) ##STR8## in which X and n have the abovementioned meanings with 1 to 1.5 times the stoichiometric amount of a carbonyl compound of the general formula (III) ##STR9## in which R.sup.1 and R.sup.2 have the abovementioned meanings or R.sup.1 and R.sup.2 together with the carbon atom of the carbonyl group can form a five- or six-membered cycloalkane ring, in an organic solvent which is inert towards the reactants under the reaction conditions at temperatures of 30.degree. to 50.degree. C., at a hydrogen superatmospheric pressure of about 0 to about 50 bar, in the presence of a sulfited platinum catalyst on activated carbon.
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