US3880859A - N-substituted-4-alkoxynaphthalimides - Google Patents

N-substituted-4-alkoxynaphthalimides Download PDF

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US3880859A
US3880859A US258060A US25806072A US3880859A US 3880859 A US3880859 A US 3880859A US 258060 A US258060 A US 258060A US 25806072 A US25806072 A US 25806072A US 3880859 A US3880859 A US 3880859A
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methanol
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Horst Scheuermann
Peter-Matthias Hell
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide

Definitions

  • R is substituted alkyl. unsubstituted or substituted cycloalkyl. aralkyl or heteroalkyl and R' is alkyl or alkyl bearing alkoxy as a substituent.
  • substituted alkyls R are linear or branched groups of up to eight carbon atoms which may be interrupted by oxygen. NH or sulfur and may bear cyano, chloro, bromo. alkoxy. aroxy, carbalkoxy, carbamoyl, N-substituted carbamoyl arylamino, dialkylamino quaternary ammonium or tertiary sulfonium as substituents.
  • Cycloalkyls R may bear alkyl as a substituent and aralkyls R may bear the substituents specified for alkyl and also N-suhstitutcd sulfonamido as substituents.
  • Hcteroalkyls may bear for example alkyl of one to four carbon atoms. cyano or carbalkoxy of up to five carbon atoms as substituents.
  • R may be where Z is hydrogen alkanoyl of two to eight carbon atoms. acetyl bearing chloro. phenyl. hydroxy, phenoxy or methoxy as a substituent benzoyl, benzoyl bearing chloro, methyl or methoxy as substituent. thenoyl or a radical of the formula R NHCO- or R"O- (O-z 5 R" is methyl. ethyl, n-propyl, isopropyl. phenyl, chlorophenyl. dichlorophenyl or methylphenyl; R is alkyl of one to eight carbon atoms, alkoxyalkyl of three to six carbon atoms.
  • A is hydrogen. methyl. phenyl or a radical of the formula CH- R; R is hydroxy. alkoxy of one to eight carbon atoms. Hmethoxyethoxy. fi-ethoxyethoxy, B-butoxyethosy. phcnoxy, phenosy bearing chloro methyl or methosy as substituents phenylmercapto. methoxyphenylmercapto or a radical of the formula R is alkyl of one to four carbon atoms or B-hydroxy c a oc a coma CEHAN CZHMJ. ⁇ /O,
  • radicals R containing sulfonium groups are suitable:
  • counterions for the ammonium and sulfonium radicals are chloride, bromide. iodide, sulfate. methosulfate, ethosulfate, benzenesulfonate and toluenesulfonate.
  • Radicals R which contain basic nitrogen and also the quaternized radicals derived therefrom are of particular significance. The following are given as examples:
  • B is alkyl of one to four carbon atoms or C H OH and X is methyl, ethyl, phenyl or henzyl,
  • radicals are suitable for Z, R, R, R and S for R methoxy. ethoxy. n-propoxy, isopropoxy. nbutoxy. isobutoxy, hexoxy and B-ethylhexoxy; for R and R": methyl. ethyl and butyl.
  • Y is a nitrogenous alkylatable radical.
  • a quaternized radical a radical containing sulfonium groups or a radical of the formula:
  • alkanoyl of two to eight car may for example be carried out for the production of the new compounds.
  • Hal is bromine or preferably chlorine.
  • N 0 Hal may be reacted with an epoxide of the formula (III (III) in which D is hydrogen. methyl or phenyl in an alcohol of the formula: ROH in which R has the above meanings to form a compound of the formula:
  • 4-methoxy-N-(B-hydroxyethoxyl-naphthalimide is prepared as follows: 24.8 parts of 4-chloro-N- hydroxynaphthalimide is suspended in 250 parts of methanol and then 30 parts of triethylamine is added. After heating for half an hour at 45 to 50C the whole is filtered and then 13.5 parts of ethylene oxide is passed into the filtrate at 50 to 60C. The whole is then heated under reflux for 6 hours and allowed to stand for 12 hours. The product is suction filtered. washed with methanol and dried. 19.5 parts (687! of theory) of a pale yellow compound is obtained which melts at from 183 to 185C.
  • EXAMPLE 2 16 parts of hydrogen bromide is passed into 180 parts of benzene and then 28.7 parts of 4 methoxy-N-(/3 hydroxyethoxyl-naphthalimide and 2 parts of pyridine are introduced. Whilst continuing to pass hydrogen bromide in. the suspension is stirred at to C for 6 hours, cooled and suction filtered, and the residue is suspended in 500 parts of water and neutralized with sodium carbonate. After suction filtration and drying. 32 parts (927: of theory) of 4-methoxy-N-(B- bromoethoxy)-naphthalirnide is obtained having a melting point of 166 to 168C. After the compound has been recrystallized from 90% acetic acid it melts at 167 to 169C.
  • EXAMPLE 3 A mixture of 350 parts of 4-methoxy-N-(B- bromoethoxy)-naphthalimide. 150 parts of chlorobenzcne and 42.5 parts of piperidine is heated for 7 hours at 80C, then cooled and the product is precipitated with petroleum ether and suction filtered. For further purification the filter cake is stirred into 1000 parts of water. again suction filtered and dried. After recrystallization from cyclohexane. 23.5 parts (66% of theory) of 4-methoxy-N-(B-piperidinoethoxy l-naphthalimide having a melting point of 126 to 128C is obtained.
  • Example 5 The compound described in Example 5 may also be 6 prepared as follows.
  • EXAMPLE 14 306 parts of 4-chloro-N-(B-methoxyethoxy)- naphthalimide is suspended in 300 parts of methanol. 70 parts of a 30% solution of sodium methylate in methanol is added and the whole is heated at 60 to 65C for 6 hours. After cooling. the product is suction filtered, washed with methanol and water and the dried product is recrystallized from toluene. 19.8 parts (659? of theory) of 4-methoxy-N-(B-methoxyethoxy naphthalimide having a melting point of 183 to 184C is obtained.
  • the 4-chloro-N-( B-methoxyethoxy )-naphthalimide required as starting material is prepared as follows: 248 parts of 4-chloro-N-hydroxynaphthalimide is suspended in 400 parts of methanol and after 21 parts of triethylamine has been added the whole is heated for half an hour at 45 to 50C. The solution is filtered and 35 parts of ,B-methoxyethyl p-toluenesulfonate is dripped into the eluate. The whole is then heated for 10 hours under reflux. allowed to cool and the product which is deposited is suction filtered and washed with methanol. The yield is 22.0 parts (72% of theory). The compound melts at 95 to 97C.
  • EXAMPLE 77 parts of sodium is added to 250 parts of methyl glycol followed by 30.6 parts of 4-chloro-N-(B- methoxyethoxy)-naphthalimide.
  • the solution is heated for thirteen hours at 90 to 110C. allowed to cool. poured into 1500 parts of water. neutralized with hydrochloric acid and stirred for another 2 hours.
  • the product is suction filtered. washed with water and dried. For purification. the product is extracted with hot toluene and. after concentration of the extract. is suction filtered. 19.0 parts (627: of theory) of 4-(8- methoxyethoxy)-N-(B-methoxyethoxy)-naphthalimide having a melting point of 192 to 194C is obtained.
  • EXAMPLE 16 In a manner analogous to that described in Example 14. 32.0 parts of 4-chloro-N-lB-ethoxyethoxy)- naphthalimide is reacted The crude product is recrystallized from isopropanol. 16.0 parts (51% of theory) of 4methoxy-N-(B-cthoxyethoxy)-naphthalimide is obtained which has a melting point of 87 to 89C.
  • 4-chloro-N-tB-cthoxyethoxy)-naphthalimide is obtained as described in Example 14 from 4-chloro-N hydroxynaphthalimide by reaction with ,B-ethoxyethyl p-toluenesulfonate. The compound melts at 68 to 71C.
  • EXAMPLE 17 70 parts of a 30% solution of sodium methylate in methanol is added to 36.8 parts of 4chloro-N-(B- phenoxyethoxy) naphthalimide which has been sus pended in 250 parts of methanol. The whole is heated for 6 hours at 60 to C and the cooled suspension is suction filtered and the product is washed with methanol and water. dried and recrystallized from butanol. 23.5 parts (65% of theory) of 4-methoxy-N-(B- phenoxyethoxyl-naphthalimide is obtained having a melting point of 133 to 134C.
  • 4-chloro-N-( ,B-phenoxyethoxy )-naphtha1imide is obtained as follows: 40 parts of triethylamine is added to 49.5 parts of 4chloro-N-hydroxynaphthalimide in 600 parts of methanol and 48 parts of B-phenoxyethyl bromide is dripped in at 60 to 65C. After heating for three hours under reflux. the whole is cooled and the precipitate is suction filtered and dried. 54 parts (747r of theory) of 4-ch
  • EXAMPLE 18 50 parts of a 30% solution of sodium methylate in methanol is added to a suspension of 33.8 parts of 4- chloro-N-benzyloxynaphthalimidc in 120 parts of methanol. After the mixture has been heated for 5 hours at 65 to C it is cooled. 200 parts of water is added and it is acidified with glacial acetic acid. The precipitate is stirred for one hour. suction filtered. washed with water and methanol and dried followed by recrystallization from methyl glycol. 27.6 parts (83% of theory) of 4-methoxy-N-benzyloxynaphthalimide having a melting point of 161 to 162C is obtained.
  • EXAMPLE 19 33.8 parts of 4-chloro-N-benzyloxynaphthalimide is added to a solution of 9.2 parts of sodium in 150 parts of methyl glycol prepared at 60 to 70C and the mixtures is heated for nine hours at to C. After cooling. 300 parts of water is added and the whole is acidified with 50 parts of glacial acetic acidv The precipitate is suction filtered, washed with water and methanol. recrystallized from methyl glycol and dried. 27.1 parts of 4-B-methoxyethoxy-N-benzyloxynaphthalimide having a melting point of 200 to 201C is obtained.
  • EXAMPLE 20 54 parts of a 30% sodium methylate solution is added to 47 parts of 4-chloro-N-(pdiethylaminosulfonylbenzyloxy)-naphthalimide in 500 parts of methanol and the whole is then heated at the boil for six hours. Suction filtration is carried out after cooling and the filter cake is washed with methanol and water and dried. 41 parts of 4-methoxy-N-(pdiethylaminosulfonylbenzyloxyJ-naphthalimide having a melting point of 172 to 174C is obtained.
  • EXAMPLE 25 46 parts of a solution of sodium methylate is added to 29 parts of 4-chloro-N-(1'-methy1imidazolyl- [2' )-methoxy )-naphtha1imide in 400 parts of methanol. The mixture is heated for 5 hours at 60 to 65C and cooled. The precipitate is suction filtered, washed with water and methanol and dried. 18 parts (63% of theory) of 4-mcthoxy-N-11'-methy1imidazolyl-(2')- methoxy )-naphtha1imide having a melting point of 245 to 246C is obtained.
  • the 4-chloro compound is obtained in a yield of 7292 from 4-ch1oro-N-hydroxynaphthalimide and l-methyl- Z-chloromethylimidazole hydrochloride in the presence ofequimolar amounts of triethylaminc in solution in methanol.
  • the compound melts at 176 to 178C.
  • EXAMPLE 26 40.5 parts of a 3091 solution of sodium methylate is added to a suspension of 283 parts of 4-ch1oro-N- lbenzimidazolyl-(Z'))-methoxynaphthalimide in 100 parts of methanol and the whole is boiled for 5 hours. After cooling. the product is suction filtered. washed with methanol and water and recrystallized from odiehlorobenzcne. 19 parts (689? of theoryl of 4- methoxy-N-(benzimidazolyH2'1) methoxynaphthalimide is obtained having a melting point of 188 to 190C.
  • EXAMPLE 27 4-methoxy-N-l l'-phenylpyrazolyl-(4 )-methoxy)- naphthalimide is prepared by analogy to Example 26.
  • the compound is recrystallized from methyl glycol and then has a melting point of 192 to 194C.
  • EXAMPLE 28 30 parts of hydrogen bromide is passed into 300 parts of benzene and then 30.1 parts of 4-methoxy-N-(B- hydroxypropoxy)-naphtha1imide and 2 parts of pyridine are introduced by the method of Example 2. While continuing to pass in hydrogen bromide. the whole is heated for 24 hours at C. After cooling, the whole is filtered and the filtrate has 300 parts of petroleum ether added to it. The product precipitated is suction filtered. suspended in 500 parts of water, neutralized with sodium carbonate, suction filtered and dried. 32.5 parts (89% of theory) of 4-methoxy-N-(B- bromopropoxy)-naphtha1imide is obtained having a melting point of 127 to 129C.
  • the 4-methoxy-N-tB-hydroxypropoxy naphthalimide required as starting material is prepared analogously to Example 1 from 24.8 parts of 4ch1oro- N-hydroxynaphthalimide and 17.5 parts of propylene oxide. 20.2 parts (67% of theory) ofa pale yellow compound is obtained which melts at 168 to 170C.
  • EXAMPLE 29 A mixture of 36.4 parts of 4-methoxy-N-(B- bromopropoxy)-naphthalimide, 39 parts of piperidine and 100 parts of methyl glycol is heated at 80C for 9 hours, cooled. 500 parts of water and 50 parts of sodium chloride are added and the whole is allowed to stand for 5 hours. After decanting, the precipitiated product is washed with water and recrystallized from cyclohexane after drying. 24.5 parts (66% of theory) of 4-methoxy-N-(B-piperidinopropoxy)-naphtha1imide having a melting point of 101 to 103C is obtained.
  • EXAMPLE 30 2.5 parts of sodium is dissolved in parts of ethanol and then 1 1 parts of thiophenol and 35 parts of 4' methoxy-N-(B-bromoethoxy)-naphthalimide are introduced. The mixture is heated for 10 hours under reflux. cooled. and the residue from suction filtration is washed with water and dried. The product is recrystallized from toluene. 17 parts (45% of theory) of 4- methox -N-( ,B-phenylmercaptoethoxy )-naphthalimide is obtained having a melting point of 109 to l 11C.
  • EXAMPLE 3 l As described in Example 30 4-methoxy-N-(B- hydroxyethylmercaptoethoxy)-naphthalimide is pre pared from 4-methoxy-N-lB-hromoethyl)naphthalimide and B-mercapto-ethanol. 34.7 parts of this com pound is dissolved in 500 parts of acetone and 25 parts of dimethyl sulfate is added. The mixture is heated for 5 hours at 60C, allowed to cool and suction filtered. The filter residue is dissolved in 250 parts of water and the filtered solution has 13.6 parts of zinc chloride added to it. After salting out with sodium chloride, the
  • Example R X Meltin point eit so to 167C Continued Example a x l-l+ :l Lint; enal 36 CH QCIIHQ-CHQ-OH 2 CH2 1:! CH2 CHE-OH ca so 202 to 205% CH2 CH2 I l c a ca so 180 to 182% 3 H ra i N ,8 Cn oH -l l u-cu l /2 zncl, 2
  • the compounds characterized by the 51 c a oe u EXAMPLE 107 55 parts of a 30% solution of sodium methylate in methanol is added to a suspension of 45 parts of 4- chloro-N-(p-morpholinocarbonylbenzyloxyJ- naphthalimidc in 500 parts of methanol and the whole is boiled under reflux for ten hours. After cooling the whole is suction filtered. the residue washed with methanol and water and the dried product is recrystallized from methyl glycol. 25 parts of 4 methoxy-N-(p morpholinocarhonylbenzyloxy)-naphthalimide is obtained having a melting point of 198 to 200C.
  • EXAMPLE 108 36 parts of styrene oxide is gradually added at 50 to 60C to 25 parts of 4-ehloronaphthalhydroxyimide dissolved in 200 parts of methanol and 30 parts oftriethylamine at the said temperature. The mixture is stirred for 10 hours at 60C, allowed to cool. and the precipitate suction filtered and washed with methanol and wa ter. The product is recrystallized from hutanol and 24 parts (66% of theory ofa mixture of compounds of the formulae:
  • OCH -caa Q e 2 t cn oa O o o ocn is obtained which has a melting point of 146 to 148C.
  • EXAMPLE 109 A mixture of 35 parts of 4-methoxy-N-(B- hromocthoxyl-naphthalimide. 42 parts of 4- mcthylpyrazolc, 14 parts of potassium carbonate and 300 parts of chlorohenzene is heated for eighteen hours at 80 to 85C. The mixture is filtered while still hot, 200 parts of petroleum ether is added to the filtrate and the deposited precipitate is suction filtered. washed with water and recrystallized from ethanol. 27 parts (77% of theory] of 4-methoxy-N-(B-(4- methylpyrazolyl l J-ethoxy)-naphthalimide is obtained having a melting point of 155 to 157C.
  • EXAMPLE 1 10 The pyridine in Example 33 is replaced by 3- methylimidazole. 42 parts (987: of theory) of the salt 3) of the formula:
  • EXAMPLE 111 The corresponding imidazolium salt is obtained with 2,3-dimethylimidazole analogously to Example 33. The compound melts at 230 to 233C with decomposition.
  • EXAMPLE 113 365 parts of 4-methoxy-N-(0chloroacetyloxyethoxy)-naphthalimide is heated in 180 parts of chlorobenzene and parts of pyridine for 15 hours at 80 to 90C. Petroleum ether is added followed by decanting. The non-crystalline residue is heated with 500 parts of water at 50C. The solution is filtered. 15 parts of zinc chloride in 50 parts of water is added. and the product is salted out. 36 parts of a pyridinium salt is obtained which contains of sodium chloride; the compound has the formula:
  • EXAMPLE 1 14 36 parts of a 3091 solution of sodium methy'late is added to 292 parts of 4-chloro-N-B-hydroxyethoxynaphthalimide in 150 parts of methanol and this mixture is heated for 3 hours at 60 to 60C. cooled. suction filtered, the precipitate washed with methanol and dried. 22.1 parts (7771 of theory) of 4-methoxy-N-fihydroxyethoxynaphthalimide is obtained having a melting point of 194 to 195C.
  • EXAMPLE 115 247.5 parts of 4 chloro-Nhydroxynaphthalimide is dissolved in a mixture of 3000 parts of methanol and 303 parts of triethy'lamine. 132 parts of ethylene oxide is passed into this solution in the course of 2 hours at is ob- 45 to 50C. The whole is stirred for another 3 hours at 45 to 50C, cooled to 15 to 20C and the deposited precipitate is suction filtered. washed with methanol and dried. 191 parts (66.5% of theory) of 4-methoxy- Nfi-hydroxyethoxynaphthalimide is obtained having a melting point of 193 to 195C.
  • EXAMPLE 116 The procedure of Example 1 15 is followed but 3000 parts of ethanol is used instead of methanol. 216 parts (729? of theory) of 4-ethoxy-N-B-hydroxyethoxynaphthalimide having a melting point of 161 to 163C is obtained under otherwise identical conditions.
  • EXAMPLE 117 The procedure of Example 1 15 is followed but 3000 parts of methyl glycol is used instead of methanol. 205 parts (627! of theory) of 4-B-methoxycthoxy-N-B- hydroxyethoxynaphthalimide is obtained having a melting point of 180 to 181C.
  • EXAMPLE 118 The procedure of Example is followed but 174 parts of propylene oxide is used instead of ethylene oxide. 235 parts (78% of theory) of 4-methoxy-N-B- hydroxypropoxynaphthalimide is obtained having a melting point of 171 to 173C.
  • EXAMPLE 119 EXAMPLE 120 The procedure of Example 1 19 is followed but 31.5 parts of p-chlorobenzoyl chloride is used instead of benzoyl chloride. The product is recrystallized from chlorobenzenc. 51 parts (80% of theory) of the compound having the following formula and which melts at 166 to 168C is obtained:
  • EXAMPLE I21 1 part of concentrated sulfuric acid is added to a solution of 28.7 parts of 4-methoxy-N-B-hydroxyethoxynaphthalimide in 150 parts of acetic anhydride and the whole is stirred for 4 hours at 50 to 55C. The mixture is then poured onto ice. stirred for another hour. and the precipitate is suction filtered and dried. After recrystallization from xylene. 30 parts (91% of theory) of 4-methoxy-N-B'acetoxyethoxynaphthalimide is obtained having a melting point of 160 to 161C.
  • EXAMPLE 122 I 0-CH -Cl-l -OC-CH -Cl o N o
  • EXAMPLE 123 parts of phenoxyaeetyl chloride is added to 2817 parts of 4-methoxy-N-B-hydroxyethoxynaphthalimide in 100 parts of nitrobenzene and this mixture is heated for 3 hours at 100 to 1 10C. The nitrobenzene is then distilled off with steam. and the residue is suction filtered and stirred for 1 hour in 100 parts of methanol followed by suction filtration. drying and recrystallization from benzene. 24.5 parts (58% of theory) of the compound of the formula:
  • EXAMPLE 124 The procedure of Example 123 is followed but 128 parts of isobutyryl chloride is used instead of phenoxyacetyl chloride. The product is recrystallized from toluene. 17.5 parts (4971 of theory) of the following compound is obtained which melts at 168 to 172C:
  • EXAMPLE 12 1 part of concentrated sulfuric acid is added to 33.1 parts of d-B-methoxyethoxy-NB-hydroxyethoxynaphthalimide in 100 parts of acetic anhydride and this mixture is stirred for 3 hours at 45 to 50C. It is then poured onto ice and the precipitate is suction filtered and recrystallized from toluene. 34 parts (91% of theory) of the compound of the formula:
  • EXAMPLE 130 A mixture of 24.8 parts of 4-chloro-N- hydroxynaphthalimide. 30 parts of triethylamine. 300 parts of methanol and 45 epoxypropane is heated for 5 hours at 60 to 65C. cooled. suction filtered and recrystallized from toluene. 264 parts (67% of theory) of the compound having a melting point of 151 to 153C described in Example 129 is obtained.
  • the compound melts at 179 to 180C.
  • EXAMPLE 132 20.3 parts of the compound described in Example 131 is dissolved in 120 parts of acetic anhydride. After 2 parts of concentrated sulfuric acid have been added the whole is stirred for 3 hours at 45 to 50C. poured onto ice and the precipitate is suction filtered and recrystallized from alcohol. 18 parts (805! of theory) of the compound of the formula:
  • EXAMPLE 138 17.2 parts of N-Z.3-epoxypropylmorpholine is added 2 1 2 5 to 24.8 parts of 4-chloro-N-hydroxynaphthalimide dis- 0 0 OH solved in a mixture of 250 parts of methanol and parts of triethylamine. After the whole has been stirred for 5 hours at to C. it is cooled, the precipitate is suction filtered, and the residue washed with methanol and dissolved in a mixture of parts of methanol CH and 36 parts of a 30% solution of sodium methylate. 3 After the solution has been heated for 3 hours at 65 to 70C it is cooled and the precipitate is suction filtered EXAMPLE I36 and recrystallized from toluene.
  • EXAMPLE 189 19.4 parts of methyl glycol chloroformate is added at phcnylethoxynaphthalimide and l 1.5 parts of pyridine in 150 parts ofmethylene chloride. The whole is stirred for another hour at 5 to C and 5 hours at to C. 200 parts of water is added. the methylene chloride phase is separated. shaken with l N hydrochloric acid and water. dried and concentrated under suhatmospheric pressure, The residue is recrystallized from toluene. 33 parts (71% of theory) of the following compound whieh melts at 132 to 134C is obtained:
  • Example R Melting point CH O l 5 ll 9 -O-CH -C1 I-OCOCH 122 to 192 W 59 -O-CH -CHOC-OCH 10 -1 to 106 -ocri cn -oEf-0ca cri ocn 87 to 89 Continued Example R Melting point CH O at O a 2390a 0c H t T 9 l D OCH CHOCOC H 1A9 to 151 llt;
  • B is alkyl of I to 4 carbon atoms taken as separate 1.
  • a compound of the formula substituents or when taken together with the nitrogen atom may also form a heterocyclic ring se- 08 lectcd from the class consisting of O, 6 O pyrrolicldinium. piperidinium and imidazolinium,
  • ⁇ and l l X is methyl. ethyl. phenyl or bcnzyl; and R is methyl or ethyl.
  • R is a radical selected from the class consisting l Hal OZ i l 1 e x K -Cl-[ CH-A -CH CHA -CH -CHN D B B 00113 wherein R is a radical selected from the class consisting of 9 i and CHZCHZ-N 5S CH2CH2 OCH3:
  • O I in which: -CH CH OCOC H A is hydrogen or methyl; Hal is chlorine or bromine; 0 CH 0 Z is alkyl of 1 to 4 carbon atoms, benzoyl alkanoyl l l CH CHOCOC H of 2 to 8 carbon atoms, the radical R NHCO where R is methyl, ethyl. n-propyl isopropyl, phenyl, chlorophenyl dichlorophenyl or methyl- H phenyl, or the radical R"OCO where R is CHZCH2 OC CSHS, alkyl of l to 8 carbon atoms. alkoxyalkyl of 3 to 6 carbon atoms cyclohexyl. bcnzyl. phenyl, chlorophenyl, methylphenyl or methoxyphenyl; D is hydrogen or methyl.

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US258060A 1971-06-03 1972-05-30 N-substituted-4-alkoxynaphthalimides Expired - Lifetime US3880859A (en)

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DE19712127522 DE2127522A1 (en) 1971-06-03 1971-06-03 Bluing agents - 4 alkoxy n alkoxy naphthalimides from 4 halo naphthalimides
DE2147706A DE2147706A1 (de) 1971-09-24 1971-09-24 Verbindungen der naphthalimidreihe

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4139532A (en) * 1976-05-14 1979-02-13 Basf Aktiengesellschaft N-Acylaminonaphthalimides
US4508900A (en) * 1980-11-03 1985-04-02 Hoechst Aktiengesellschaft Cationic compounds of the naphthalimide series, process for their preparation and their use
US4595756A (en) * 1982-09-13 1986-06-17 Hoechst Aktiengesellschaft Cationic compounds of the naphthalimide series, process for their preparation and their use
US4841052A (en) * 1986-02-15 1989-06-20 Bayer Aktiengesellschaft Naphthalic acid imides electrophotographic toners
US6177423B1 (en) 1996-11-01 2001-01-23 Warner-Lambert Company Isoquinolones
US6391062B1 (en) 1999-02-09 2002-05-21 L'oreal S.A. Use of cationic fused polycyclic compounds for dyeing keratin substances, dye compositions and dyeing processes
US10113031B2 (en) * 2013-11-01 2018-10-30 Lubrizol Advanced Materials, Inc. Aromatic dispersant composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2231609C3 (de) * 1972-06-28 1980-09-04 Basf Ag, 6700 Ludwigshafen Verbindungen der Naphthalimidreihe

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2231495A (en) * 1938-07-27 1941-02-11 Gen Aniline & Film Corp Vat-dyestuffs of the naphthalimide series and a process of preparing them
US3312706A (en) * 1963-02-14 1967-04-04 Dow Chemical Co Phosphoramidothioates
US3330834A (en) * 1967-07-11 Naphthalimide whitening agents anb method of making same
US3357985A (en) * 1965-07-30 1967-12-12 Hoechst Ag Benzothioxanthene dicarboxylic acid imide dyestuffs
US3367937A (en) * 1964-08-07 1968-02-06 Hoechst Ag Benzothioxanthene dicarboxylic acid imide dyestuffs
US3502678A (en) * 1965-08-12 1970-03-24 Hoechst Ag Nitrobenzothioxanthene dicarboxylic acid imide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3330834A (en) * 1967-07-11 Naphthalimide whitening agents anb method of making same
US2231495A (en) * 1938-07-27 1941-02-11 Gen Aniline & Film Corp Vat-dyestuffs of the naphthalimide series and a process of preparing them
US3312706A (en) * 1963-02-14 1967-04-04 Dow Chemical Co Phosphoramidothioates
US3367937A (en) * 1964-08-07 1968-02-06 Hoechst Ag Benzothioxanthene dicarboxylic acid imide dyestuffs
US3357985A (en) * 1965-07-30 1967-12-12 Hoechst Ag Benzothioxanthene dicarboxylic acid imide dyestuffs
US3502678A (en) * 1965-08-12 1970-03-24 Hoechst Ag Nitrobenzothioxanthene dicarboxylic acid imide

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4139532A (en) * 1976-05-14 1979-02-13 Basf Aktiengesellschaft N-Acylaminonaphthalimides
US4508900A (en) * 1980-11-03 1985-04-02 Hoechst Aktiengesellschaft Cationic compounds of the naphthalimide series, process for their preparation and their use
US4595756A (en) * 1982-09-13 1986-06-17 Hoechst Aktiengesellschaft Cationic compounds of the naphthalimide series, process for their preparation and their use
US4841052A (en) * 1986-02-15 1989-06-20 Bayer Aktiengesellschaft Naphthalic acid imides electrophotographic toners
US6177423B1 (en) 1996-11-01 2001-01-23 Warner-Lambert Company Isoquinolones
US6391062B1 (en) 1999-02-09 2002-05-21 L'oreal S.A. Use of cationic fused polycyclic compounds for dyeing keratin substances, dye compositions and dyeing processes
US10113031B2 (en) * 2013-11-01 2018-10-30 Lubrizol Advanced Materials, Inc. Aromatic dispersant composition

Also Published As

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BE784351A (fr) 1972-12-04
IT958187B (it) 1973-10-20
FR2140087B1 (enrdf_load_stackoverflow) 1978-03-17
GB1391657A (en) 1975-04-23
FR2140087A1 (enrdf_load_stackoverflow) 1973-01-12

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