Process for preparing polycyclic dyes

Details Process for preparing polycyclic dyes Process for preparing polycyclic dyes

1995-05-25

1997-09-02

McKane, Joseph

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30777

Patent

active

056633718

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/GB93/02296 filed Nov. 8, 1993.
The present invention relates to a process for the preparation of certain polycyclic dyes and to certain intermediates used the process.
According to the present invention there is provided a process for the preparation of a polycyclic dye of the Formula (1): ##STR3## by reacting a compound of Formula (2): ##STR4## with a compound of Formula (3): ##STR5## wherein: Ring A is unsubstituted or is substituted by from 1 to 5 groups; optionally substituted aralkyl, and R.sup.1 and R.sup.2 each independently is --H, alkyl, aryl or aralkyl.
Where Ring A and Ring B are substituted by from 1 to 5 groups each group independently is selected from alkyl; alkoxy; alkoxyalkyl; alkoxyalkoxy; alkylcarbonyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; alkylcarbonyloxyalkoxy; alkoxyalkoxycarbonylalkoxy; alkenyl; cyanoalkyl; cyanoalkoxy; hydroxyalkyl; hydroxyalkoxy; halogen, especially chlorine or bromine; hydroxy; cyano; nitro; alkylthio; arylthio; aryl; aryloxy; alkylsulphonyl; arylsulphonyl; --NH.sub.2 ; --NHalkyl; --N(alkyl).sub.2 ; --NHCOalkyl and --NHSO.sub.2 alkyl; and preferably such groups in which each alkyl is C.sub.1-4 -alkyl, each alkoxy is C.sub.1-4 -alkoxy, the alkenyl is C.sub.2-4 -alkenyl and each aryl is phenyl.
Ring A is preferably unsubstituted or is substituted by groups selected from alkyl; alkoxy; alkoxyalkyl; alkoxyalkoxy; alkylcarbonyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; alkylcarbonyloxyalkoxy; alkoxyalkoxycarbonylalkoxy; alkenyl; cyanoalkyl; cyanoalkoxy; hydroxyalkyl; hydroxyalkoxy; halogen, especially chlorine or bromine; hydroxy; cyano; nitro; aryl; aryloxy; alkylsulphonyl and arylsulphonyl; and preferably such groups in which each alkyl is C.sub.1-4 -alkyl, each alkoxy is C.sub.1-4 -alkoxy, the alkenyl is C.sub.2-4 -alkenyl and each aryl is phenyl, Ring A is more preferably unsubstituted or is substituted by groups selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and C.sub.2-4 -alkenyl, and Ring A is especially unsubstituted or is substituted by C.sub.1-4 -alkoxy.
Ring B is preferably substituted by groups selected from --NO.sub.2, C.sub.1-4 -alkoxy, C.sub.1-4 -alkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, C.sub.2-4 -alkenyl and C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkoxy, Ring B is more preferably substituted by groups selected from --NO.sub.2, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2 and C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkoxy and especially substituted by groups selected from --NO.sub.2 and C.sub.1-4 -alkyl.
Ring A is preferably unsubstituted or is substituted by from 1 to 3 groups and more preferably is unsubstituted or is substituted by 1 or 2 groups and especially is unsubstituted or is substituted by 1 group.
Where Ring A is substituted by 1 group this group is preferably in the 4-position, where Ring A is substituted by 2 groups these are preferably in the 3- and 4-positions and where Ring A is substituted by 3 groups these are preferably in the 3-, 4- and 5-positions.
Ring B is preferably substituted by from 1 to 3 groups and more preferably by 1 or 2 groups.
Where Ring B is substituted by 1 group this is preferably in the 4-position and where Ring B is substituted by 1 or 2 groups these are preferably in the 3- and 4-positions.
It is especially preferred that Ring A is unsubstituted or is substituted in the 4-position by C.sub.1-4 -alkoxy. It is especially preferred that Ring B is substituted in the 4-position by --NO.sub.2, C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyl or C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkoxy; or that Ring B is substituted in the 4-position by --NO.sub.2, C.sub.1-4 -alkoxy or C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl-C.sub.1-4 -alkoxy and in the 3-position by C.sub.1-4 -alkyl.
Ring B is preferably 4-nitrophenyl and more preferably 3-alkyl-4-nitrophenyl and especially 3-methyl-4-nitrophenyl or 3-ethyl-4-nitrophenyl.
The halogen represented by X and X.sup.1 is preferably --F, --Cl or --Br, more preferab

REFERENCES:
patent: 5214161 (1993-05-01), Milner
Chemical Abstracts, vol. 91, No. 1, Jul. 1979, Pluman et al: "Alpha-dichlorobenzyl cyanide, a nieuw reagent for aromatic chlorination", p. 470, see abstract, & Pol,J.Chem. vol. 53, No. 1, @ 1979, pp. 201-203.

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