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US 5,183,888 AGranted
Polycyclic dyes
AssigneeImperial Chemical Industries PLC
InventorsRonald W. Kenyon, David F. Newton, Derek Thorp
Life of this patent
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Abstract
The present invention relates to a process for the preparation of certain polycyclic dyes and in particularly the preparation of a polycyclic dye of Formula I: ##STR1## By reacting a phenyltartronic acid of Formula II: ##STR2## With either a compound of Formula III: ##STR3## or a compound of Formula IV: ##STR4##
Claims1
A process for the preparation of a polycyclic dye of Formula I:
- ##STR17## by reacting a phenyltartronic acid of Formula II:
- ##STR18## wherein:
- W is --NR.sup.1 R.sup.2 or --OR.sup.3 ;
- R.sup.3 is H or C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl or phenyl-C.sub.1-4 -alkylene group each of which is unsubstituted or is substituted by a group selected from alkyl, alkoxy, nitro, halogen, alkoxyalkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, alkylcarbonyl, alkoxycarbonyl, alkoxyalkoxy carbonyl, alkoxycarbonyloxy, alkoxyalkoxycarbonyloxy, alkylcarbonyloxy, cyano and amino in which each alkyl is C.sub.1-4 -alkyl;
- R.sup.1 & R.sup.2 are each independently H or C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl, phenyl-C.sub.1-4 -alkylene or phenyl group each of which is unsubstituted or is substituted by a group selected from alkyl, alkoxy, nitro halogen, alkoxyalkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, alkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonyloxy, alkoxyalkoxycarbonyloxy, alkylcarbonyloxy, cyano and amino in which each alkyl is C.sub.1-4 -alkyl;
- or
- R.sup.1 & R.sup.2 together with the nitrogen atom to which they are attached from a piperidino or morpholino group;
- or
- R.sup.1 or R.sup.2 together with the nitrogen atom and the adjacent carbon atom of Ring B form a tetrahydroquinolinyl group;
- and
- Ring B is unsubstituted, apart from the group W, or is substituted by from one or two further groups selected from alkyl;
- alkenyl;
- alkoxy;
- alkoxyalkoxy;
- alkoxycarbonyalkoxy;
- alkoxyalkoxycarbonyl alkoxy;
- alkylcarbonyloxyalkoxy;
- cyanoalkoxy;
- hydroxyalkoxy;
- chlorine;
- bromine;
- hydroxy;
- alkylthio;
- arylthio;
- aryloxy;
- alkylcarbonyl and alkylsulphonyl;
- in which the alkyl or alkenyl contains up to 4 carbon atoms and the aryl is phenyl;
- with either (a) a compound of Formula III:
- ##STR19## wherein, Z.sup.1 & Z.sup.2 are each --O--;
- X.sup.1 & X.sup.2 are each independently selected from H, halogen, cyano, alkyl, aryl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester;
- &
- Ring A is unsubstituted or is substituted by from one to three groups selected from alkyl;
- alkenyl;
- alkoxy;
- alkoxyalkoxy;
- alkoxycarbonylalkoxy;
- alkoxyalkoxycarbonylalkoxy;
- alkylcarbonyloxyalkoxy;
- cyanoalkoxy;
- hydroxyalkoxy;
- chlorine;
- bromine;
- hydroxy;
- akylthio;
- arylthio;
- aryloxy;
- alkylcarbonyl and alkylsulphonyl;
- in which the alkyl or alkenyl contains up to 4 carbon atoms and the aryl is phenyl;
- NHCOC.sub.1-4 -alkyl;
- --NHSO.sub.2 C.sub.1-4 -alkyl;
- NR.sup.1 R.sup.2 and OR.sup.3, wherein R.sup.1, R.sup.2 and R.sup.3 are as hereinbefore defined;
- or (b) a compound of Formula IV:
- ##STR20## wherein Z.sup.1, Z.sup.2, X.sup.1 and X.sup.2 are as hereinbefore defined;
- and oxidation of the intermediate compound to dehydrogenate the peripheral heterocyclic rings.
51 more elements
Dependencies are inferred from the claim text.