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US 3,944,553 AGranted
Bis quinoline peri acids
AssigneeTRW Inc.
InventorMichael K. O'Rell
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Abstract
Preparation of a novel heterocyclic peri acid is initiated by reacting diaminodimethylbiphenyl with methyl vinyl ketone to produce tetramethyl biquinoline. The substituent methyl groups are oxidized subsequently to produce a tetraacid, or upon dehydration of the tetraacid, a dianhydride. The peri acids of this invention have the following structural formula: ##SPC1## Where R may be either ##EQU1## or (--COOH).sub.2 and R' is --H, --OCH.sub.3, ##SPC2##
Claims3
A compound having the structure:
- ##SPC8##
- where R is selected from the group consisting of ##EQU2## and (--COOH).sub.2 and R' is selected from the group consisting of --H, ##SPC9##
- and --OCH.sub.3.
A process for the preparation of a compound having the structure:
- ##SPC10##
- where R is selected from the group consisting of:
- ##EQU3## and (--COOH).sub.2 wherein:
- A. an aminonitrotoluene is reacted with potassium iodide to produce a corresponding halonitrotoluene;
- B. heating said halonitrotoluene in the presence of powdered copper to produce a corresponding dimethyldinitrobiphenyl;
- C. hydrogenating said dimethyldinitrobiphenyl in the presence of a Raney nickel catalyst to produce a corresponding diamino dimethylbiphenyl;
- D. reacting said diamino dimethylbiphenyl with methyl vinyl ketone in the presence of inorganic metal chlorides selected from the group consisting of ferric chloride and zinc chloride to yield tetramethylbiquinoline;
- E. reacting tetramethylbiquinoline with aqueous dichromate to produce the corresponding tetracarboxybiquinoline;
- and
- F. dehydrating said tetracarboxybiguinoline to the corresponding tetracarboxybiquinoline dianhydride by heating or using a dehydrating agent selected from the group of acetic anhydride wherein each of the above steps includes isolation of the product of each step.
7 more elements
A process for the preparation of a compound having the structure:
- ##SPC11##
- comprising the steps of reacting stoichiometric amounts according to the following:
- ##SPC12##
- wherein each of the above steps includes isolation of the product of each step.
1 more element
Dependencies are inferred from the claim text.