Preparation process of benzodifuranone dyes

Details Preparation process of benzodifuranone dyes Preparation process of benzodifuranone dyes

1998-12-30

2000-01-11

Owens, Amelia

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 60, 548202, 548204, 548206, 548214, 5462844, 546341, 562441, C07D40714, C07D40900, C07C22900

Patent

active

060138114

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a process for the preparation of polycyclic dyes, particularly benzodifuranone dyes, to trihydroxydicarboxylic acids and to a process for their preparation.
According to the present invention, there is provided a process for the preparation of a polycyclic dye of Formula (1): ##STR1## which comprises the steps: i) reaction of a compound of Formula (2): ##STR2## with a compound of Formula (3): ##STR3## or a derivative thereof to form an intermediate of Formula (4): ##STR4## and ii) reaction of the intermediate of Formula (4) with an aromatic compound of Formula (5):
A and B each independently is preferably optionally substituted phenyl or naphthyl but may also be an optionally substituted heterocyclic aromatic radical such as pyridyl, thienyl, thiazolyl or isothiazolyl.
Where X.sup.1 or X.sup.2 is halo it is preferably --F, --Cl or --Br. Where X.sup.1 or X.sup.2 is alkyl it is preferably straight or branched chain C.sub.1-6 -alkyl. Where X.sup.1 or X.sup.2 is alkoxy, it is preferably straight or branched chain C.sub.1-6 -alkoxy. X.sup.1 and X.sup.2 are preferably --H.
Where A and B are substituted the optional substituents may be selected from alkyl; alkenyl; alkoxy; alkoxyalkyl; alkoxyalkoxy; alkylcarbonyl; alkoxycarbonyl; alkoxycarbonylalkoxy; alkoxyalkoxycarbonylalkoxy; cyanoalkyl; cyanoalkoxy; hydroxyalkyl; hydroxyalkoxy; haloalkyl, especially fluoro-, chloro- or bromoalkyl; haloalkoxy, especially fluoro-, chloro- or bromoalkoxy; alkythio; arylthio; aryloxy; alkylsulphonyl; arylsulphonyl; halo, especially chloro or bromo; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; cycloalkylamino; alkylcarbonylamino; arylcarbonylamino; alkylsulphonylamino; arylsulphonylamino; cycloalkyl; and alkylamino and dialkylamino substituted by --CN, --Cl, --F, --Br, --OH, --COOC.sub.1-4 -alkyl, --COOC.sub.1-4 -alkylOC.sub.1-4 -alkyl, -phenyl, --OCOC.sub.1-4 -alkyl; and preferably such groups in which the alkyl or alkoxy contains from 1 to 8 carbon atoms, especially from 1 to 4 carbon atoms; the alkenyl contains from 2 to 6 carbon atoms, especially from 2 to 4 carbon atoms; the aryl is phenyl or naphthyl and the cycloalkyl contains from 3 to 8 carbon atoms, more preferably from 4 to 6 carbon atoms and especially 6 carbon atoms. Each alkyl, alkoxy or alkenyl may be straight or branched chain alkyl, alkoxy or alkenyl respectively.
Where A or B is phenyl it is preferably unsubstituted or substituted by from 1 to 5, more preferably by from 1 to 3 of the optional substituents described above. Where A or B is phenyl and one substituent group is present, this is more preferably in the 4-position. Where 2 substituent groups are present, they are preferably in the 3- and 4-positions and where 3 substituent groups are present, they are preferably in the 3-, 4- and 5-positions.
The optional substituents for A and B are preferably selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, hydroxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonylC.sub.1-4 -alkoxy, amino, C.sub.1-4 -alkylamino and (C.sub.1-4 -alkyl).sub.2 amino and combinations thereof.
Suitable derivatives of compounds of Formula (3) include compounds in which the aldehyde group and/or the acid group are protected, preferably oxime, nitrile, --CCl.sub.3 and ester derivatives.
The first step of the process may be carried out in a liquid medium. Suitable liquid media include water, alkanols, such as methanol, ethanol or propanol, dimethyl formamide and tetrahydrofuran or combinations thereof. The liquid medium preferably contains a base. Suitable bases may be inorganic or organic and include alkali metal hydroxides such as sodium or potassium hydroxide, alkali metal carbonates and bicarbonates, such as sodium or potassium bicarbonate and sodium or potassium hydrogen carbonates, nitrogen containing bases such as mono-, di and tri-alkylamines, pyrrolidines and metal hydrides such as sodium hydride.
The liquid medium is preferably water, water/alkanol, such as water/methanol which contains an alkali metal hydroxide such as sodium or potassium hydrox

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