NO803010L - PROCEDURE FOR THE PREPARATION OF 3- (4-PYRIDINYL) ANILIN FROM 3- (4-PYRIDINYL) -2-CYCLOHEXE-1-ON-OXIM. - Google Patents

PROCEDURE FOR THE PREPARATION OF 3- (4-PYRIDINYL) ANILIN FROM 3- (4-PYRIDINYL) -2-CYCLOHEXE-1-ON-OXIM.

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Publication number
NO803010L
NO803010L NO803010A NO803010A NO803010L NO 803010 L NO803010 L NO 803010L NO 803010 A NO803010 A NO 803010A NO 803010 A NO803010 A NO 803010A NO 803010 L NO803010 L NO 803010L
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Norway
Prior art keywords
pyridinyl
oxime
acetic anhydride
aniline
approx
Prior art date
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NO803010A
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Norwegian (no)
Inventor
Rudolf Oesterlin
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Sterling Drug Inc
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Publication date
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Publication of NO803010L publication Critical patent/NO803010L/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Foreliggende oppfinnelse vedrører en forbedret fremgangsmåte til fremstilling av 3-(4-pyridinyl)anilin, The present invention relates to an improved process for the production of 3-(4-pyridinyl)aniline,

et mellomprodukt for fremstilling av rosoksacin, et anti-bakterielt middel. an intermediate for the manufacture of rozoxacin, an anti-bacterial agent.

US patenter nr. 4 026 900 og 4 075 217 beskriver oppvarming av oksim-forbindelsen av 3-(4-pyridinyl)-2-cykloheksen-1-on med et acetyleringsmiddel for dannelse av det resulterende O-acetyloksim og deretter oppvarming av O-acetyloksimforbindelsen under sure betingelser, fortrinnsvis i nærvær av en sterk mineralsyre. Acetyleringen og de etterfølgende oppvarmingstrinn foretas fortrinnsvis i kombi-nasjon ved oppvarming av oksim-forbindelsen med eddiksyre, eddiksyreanhydrid og hydrogenhalogenid, fortrinnsvis hydro-genkloridgass. Reaksjonen utføres i området på ca. 80-140°C, fortrinnsvis 100-120°C. N-acetyl-3-(4-pyridinyl)anilin-forbindelsen hydrolyseres deretter for dannelse av 3-(4-pyridinyl)anilin, et mellomprodukt for fremstilling av rosoksacin. US Patent Nos. 4,026,900 and 4,075,217 describe heating the oxime compound of 3-(4-pyridinyl)-2-cyclohexen-1-one with an acetylating agent to form the resulting O-acetyl oxime and then heating the O- the acetyl oxime compound under acidic conditions, preferably in the presence of a strong mineral acid. The acetylation and the subsequent heating steps are preferably carried out in combination by heating the oxime compound with acetic acid, acetic anhydride and hydrogen halide, preferably hydrogen chloride gas. The reaction is carried out in the area of approx. 80-140°C, preferably 100-120°C. The N-acetyl-3-(4-pyridinyl)aniline compound is then hydrolyzed to form 3-(4-pyridinyl)aniline, an intermediate for the preparation of rosoxacin.

Newman og Hung (J. Org. Chem. 38, 4073-4074 (1973)) viste omdannelse av bestemte oksimer av a-tetraloner (7-metyl- og 7-klor-a-tetraloner) til de tilsvarende N-(1-naftyl)acetamider ved oppvarming av oksim-forbindelsen i eddiksyreanhydrid og vandig fosforsyre ved 80°C i 30 min. Newman and Hung (J. Org. Chem. 38, 4073-4074 (1973)) showed the conversion of certain oximes of α-tetralones (7-methyl- and 7-chloro-α-tetralones) to the corresponding N-(1- naphthyl)acetamides by heating the oxime compound in acetic anhydride and aqueous phosphoric acid at 80°C for 30 min.

Man fikk mislykkede resultater på grunn av syrereaksjonerUnsuccessful results were obtained due to acid reactions

ved bruk av disse reaksjonsbetingelser med oksim-forbindelsen av 6-metoksy-a-tetralon. Fosforpentoksyd ble benyttet for å fremstille den vannfrie fosforsyren. using these reaction conditions with the oxime compound of 6-methoxy-α-tetralone. Phosphorus pentoxide was used to prepare the anhydrous phosphoric acid.

Foreliggende oppfinnelse angår en forbedring ved fremgangsmåten for omdannelse av 3-(4-pyridinyl)2-cyklo-heksen-1-on-oksim til 3-(4-pyridinyl)anilin, og forbedringen omfatter at man oppvarmer nevnte oksim-forbindelse med et overskudd av hver av eddiksyreanhydrid og vannfri fosforsyre, avdestillerer eddiksyren som dannes ved reaksjonen og hydrolyserer deretter N-acetyl-3-(4-pyridinyl)anilin. The present invention relates to an improvement in the process for converting 3-(4-pyridinyl)2-cyclo-hexen-1-one-oxime to 3-(4-pyridinyl)aniline, and the improvement comprises heating said oxime compound with a excess of each of acetic anhydride and anhydrous phosphoric acid, distills off the acetic acid formed by the reaction and then hydrolyzes N-acetyl-3-(4-pyridinyl)aniline.

Oppfinnelsen ligger i en forbedring av fremgangsmåten til fremstilling av 3-(4-pyridinyl)anilin, ved acetylering av 3-(4-pyridinyl)-2-cykloheksen-1-oksim for dannelse av det tilsvarende O-acetyloksim og oppvarming av denne forbindelsen under sure betingelser, idet nevnte forbedring består i oppvarming av 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim med et overskudd av eddiksyreanhydrid og vannfri fosforsyre, avdestillering av eddiksyre-biproduktet og overskudd eddiksyreanhydrid, og hydrolysering av det resterende N-acetyl-3-(4-pyridinyl)anilin under alkaliske betingelser. The invention lies in an improvement of the process for the production of 3-(4-pyridinyl)aniline, by acetylating 3-(4-pyridinyl)-2-cyclohexene-1-oxime to form the corresponding O-acetyl oxime and heating this compound under acidic conditions, said improvement consisting in heating 3-(4-pyridinyl)-2-cyclohexen-1-one-oxime with an excess of acetic anhydride and anhydrous phosphoric acid, distilling off the acetic acid by-product and excess acetic anhydride, and hydrolyzing it residual N-acetyl-3-(4-pyridinyl)aniline under alkaline conditions.

I en foretrukken utførelse utføres første trinnet i fremgangsmåten under anvendelse av ca. 7-10 mol-ekvivalenter eddiksyreanhydrid og ca. 3-10 mol-ekvivalenter vannfri fosforsyre pr. mol-ekvivalent oksim og oppvarming av reaktantene ved ca. 90-120°C, fortrinnsvis 95-120°C. In a preferred embodiment, the first step in the method is carried out using approx. 7-10 mole equivalents of acetic anhydride and approx. 3-10 mole equivalents of anhydrous phosphoric acid per mol-equivalent oxime and heating the reactants at approx. 90-120°C, preferably 95-120°C.

Den vannfrie fosforsyren som benyttes i fremgangsmåten ble fremstilt ved dehydratisering av 85% fosforsyre ved omsetning derav med eddiksyreanhydrid. The anhydrous phosphoric acid used in the method was produced by dehydrating 85% phosphoric acid by reacting it with acetic anhydride.

Det første trinnet i prosessen kan foretas ved benyttelse av mer eddiksyreanhydrid og vannfri fosforsyre, nemlig opptil ca. 15-20 mol-ekvivalenter av hver pr. mol-ekvivalent oksim, men ikke med noen spesiell fordel. The first step in the process can be carried out by using more acetic anhydride and anhydrous phosphoric acid, namely up to approx. 15-20 mole equivalents of each per molar equivalent oxime, but not with any particular advantage.

Det andre trinnet utføres hensiktsmessig under anvendelse av et vandig alkalimetallhydroksyd, fortrinnsvis natriumhydroksyd. The second step is conveniently carried out using an aqueous alkali metal hydroxide, preferably sodium hydroxide.

Følgende eksempler illustrerer oppfinnelsen ytter-ligere . The following examples further illustrate the invention.

3- ( 4- pyridinyl) anilin, alternativt betegnet 3-(4-pyridinyl)benzenamin. Vannfri fosforsyre ble fremstilt ved tilsetning av 1020 g (10 mol, d 1,082, 940 ml ) eddiksyreanhydrid til 540 g (4,68 mol, 1,7, 320 ml) av kraftig omrørt 85% fosforsyre i løpet av 20 min. under opprettholdelse av temperaturen nær 50°C med avkjøling av og til. Til den klare, varme oppløsning ble det tilsatt 188 g (1 mol) 3-(4-pyridiny2)-2-cykloheksen-1-on-oksim i en porsjon. Den innledningsvis klare, gule oppløsning ble oppvarmet på et dampbad til ca. 95°C hvor dampen var avstengt. Ved dette punkt begynte reaksjonsblandingen å skille seg i to lag, og dannet til slutt 3-(4-pyridinyl)aniline, alternatively called 3-(4-pyridinyl)benzenamine. Anhydrous phosphoric acid was prepared by adding 1020 g (10 mol, d 1.082, 940 ml) of acetic anhydride to 540 g (4.68 mol, 1.7, 320 ml) of vigorously stirred 85% phosphoric acid over 20 min. while maintaining the temperature close to 50°C with occasional cooling. To the clear, warm solution was added 188 g (1 mol) of 3-(4-pyridiny2)-2-cyclohexen-1-one-oxime in one portion. The initially clear, yellow solution was heated on a steam bath to approx. 95°C where the steam was shut off. At this point, the reaction mixture began to separate into two layers, eventually forming

et mobilt vann-hvitt øvre lag og en gul-brun viskøs gummi. Den indre temperatur i reaksjonsblandingen ble gradvis øket til ca. 110-120°C. Såsnart temperaturen begynte å synke, fikk damp på nytt virke i 90 min.. Den dannede eddiksyre (fargeløst øvre lag, 650-700 ml) ble deretter fjernet ved vakuumdestillasjon fulgt av fjerning av overskudd eddiksyreanhydrid i. vakuum. Den kontinuerlig omrørte og oppvarmede viskøse rest ble lett oppløst i 500 ml varmt vann. Den klare, mørke oppløsningen ble behandlet gradvis og under sporadisk avkjøling med ca. 800 ml 35% vandig natriumhydroksyd ved 60-80°C til en svakt basisk pH-verdi (8-9). Noe utfelt fast stoff ble oppløseliggjort ved tilsetning av 500 ml etanol a mobile water-white upper layer and a yellow-brown viscous gum. The internal temperature in the reaction mixture was gradually increased to approx. 110-120°C. As soon as the temperature began to drop, steam was again allowed to act for 90 min. The acetic acid formed (colorless upper layer, 650-700 ml) was then removed by vacuum distillation followed by removal of excess acetic anhydride in vacuo. The continuously stirred and heated viscous residue was easily dissolved in 500 ml of hot water. The clear, dark solution was treated gradually and under occasional cooling with approx. 800 ml of 35% aqueous sodium hydroxide at 60-80°C to a slightly basic pH value (8-9). Some precipitated solid was solubilized by adding 500 ml of ethanol

og oppvarming til 80°C. Det fargeløse, viskøse nedre lag inneholdende for det meste fosfatsalter ble fjernet mens det fremdeles var i varm tilstand (1 liter, 1430 g); det størknet ved omgivelsestemperatur. Til den resterende mørke oppløsning ble det tilsatt 320 ml 35% vandig natriumhydroksyd og den resulterende to-fasereaksjonsblanding ble oppvarmet ved tilbakeløp natten over (ca. 16 timer). Den mørke, homo-gene oppløsning ble avkjølt til 5°C. Det krystalliserte faste stoff ble filtrert, presset godt og deretter vasket med en minimum mengde (en mengde som akkurat dekket det faste stoff) av is-metanol og avkjølt 50% vandig etanol. and heating to 80°C. The colorless, viscous lower layer containing mostly phosphate salts was removed while still hot (1 liter, 1430 g); it solidified at ambient temperature. To the remaining dark solution was added 320 ml of 35% aqueous sodium hydroxide and the resulting two-phase reaction mixture was heated at reflux overnight (about 16 hours). The dark, homogeneous solution was cooled to 5°C. The crystallized solid was filtered, pressed well, and then washed with a minimum amount (an amount that just covered the solid) of ice-methanol and chilled 50% aqueous ethanol.

For å fjerne eventuelle resterende uorganiske salter i filterkaken, ble det faste stoff vasket gjentatte ganger med varmt vann (ca. 35-50°C). Resten ble tørket i vakuum ved 60°C og ga 134,5 g (79%) av det ønskede beige-fargede produkt, 3-(4-pyridinyl)anilin, smp. 168-171°C; enkel flekk ved tynnsjiktskromatografi (silisiumdioksyd; CHCl^: CH^OH: i-C3H7NH290:5:5; UV). To remove any remaining inorganic salts in the filter cake, the solid was washed repeatedly with hot water (about 35-50°C). The residue was dried in vacuo at 60°C to give 134.5 g (79%) of the desired beige-colored product, 3-(4-pyridinyl)aniline, m.p. 168-171°C; single spot by thin-layer chromatography (silica; CHCl^: CH^OH: i-C3H7NH290:5:5; UV).

Eksem<pel>_<2>Example<pel>_<2>

3-( 4- pyridinyl) anilin ble fremstilt i sammenlignbart utbytte i et laboratorieprøveanlegg under anvendelse av samme metode, som følger: Eddiksyreanhydrid, 55 kg, ble tilført til en glassforet reaktor med kapasitet 113,6 liter i en destil-lasjonsenhet. Fosforsyren ble tilsatt i løpet av j time idet 3-(4-pyridinyl)aniline was prepared in comparable yields in a laboratory pilot plant using the same method, as follows: Acetic anhydride, 55 kg, was fed to a 113.6 liter capacity glass-lined reactor in a distillation unit. The phosphoric acid was added over the course of j hour

temperaturen steg til 100°C. Oppløsningen ble oppvarmet til 120°C og dampen avstengt. En oppløsning av 14,6 kg oksim i 36 liter eddiksyre ble tilsatt med en slik hastighet at til-bakeløpskokingen ble opprettholdt, men uten å bevirke destillasjon. Omtrent 3/4 av oppløsningen ble tilsatt i løpet av halvannen time, hvilket resulterte i en full kjele. Trykk-damp (15,75-18 kg) ble benyttet for å begynne destillasjonen aveddiksyre. Etter\time var det plass i kjelen, og den resulterende oksimoppløsning ble langsomt tilsatt under opprettholdelse av destillasjon. Det klare eddiksyrelag ble avdestillert ved atmosfæretrykk i løpet av 2 timer, hvilket etterlot en mørk og viskøs, men omrørbar rest ved 120°C. Vakuum ble påført gradvis for å fjerne resterende eddiksyre og eddiksyreanhydrid, idet kolbe-temperaturen ble holdt over 100°C. Mens resten ble omrørt ved 100°C ("heat off"), ble 20 liter vann tilsatt i løpet av 5 min.. Temperaturen falt til 85°C, men omrøringen ble opprettholdt. Kjelen ble avkjølt med vann til 60°C og 54 kg 35% vandig natriumhydroksyd ble tilsatt i løpet av \ time, temperatur 50-65°C. Etanol, 20 liter, ble tilsatt og blandingen avkjølt til 30°C før den fikk separere. Et klart, vandig lag, 66 liter, ble avtatt og det meget mørke organiske lag, 56 liter, ble overført til en rustfri stålkjele. 35% vandig natriumhydroksyd, 34 kg, ble tilsatt til kjelen og blandingen tilbakeløpskokt (83°C) i 12 timer. Om morgenen ble blandingen avkjølt fra 60 til 5°C før filtrering. De mørke, faste stoffene ble vasket med 3x6 liter kald 25% etanol, og dette ga et lysebrunt produkt. Den våte kaken ble oppslemmet i 40 liter vann ved 30°C i h time og refiltrert. De faste stoffene ble vasket godt med vann og tørket ved 60°C i luft natten over. Dette ga 10,08 kg, eller 10080/77,8 x 170 = 76,3% av det teoretiske utbytte, av det lysebrune produkt, 3-(4-pyridinyl)anilin, smp. 165-167°C. the temperature rose to 100°C. The solution was heated to 120°C and the steam shut off. A solution of 14.6 kg of oxime in 36 liters of acetic acid was added at such a rate that reflux was maintained, but without effecting distillation. About 3/4 of the solution was added over the course of an hour and a half, resulting in a full kettle. Pressurized steam (15.75-18 kg) was used to begin the distillation of acetic acid. After \hour there was room in the kettle, and the resulting oxime solution was slowly added while maintaining distillation. The clear acetic acid layer was distilled off at atmospheric pressure over 2 hours, leaving a dark and viscous but stirrable residue at 120°C. Vacuum was applied gradually to remove residual acetic acid and acetic anhydride, keeping the flask temperature above 100°C. While the residue was stirred at 100°C ("heat off"), 20 liters of water were added over 5 min. The temperature dropped to 85°C, but stirring was maintained. The boiler was cooled with water to 60°C and 54 kg of 35% aqueous sodium hydroxide was added over 1 hour, temperature 50-65°C. Ethanol, 20 liters, was added and the mixture cooled to 30°C before being allowed to separate. A clear aqueous layer, 66 liters, was withdrawn and the very dark organic layer, 56 liters, was transferred to a stainless steel kettle. 35% aqueous sodium hydroxide, 34 kg, was added to the kettle and the mixture refluxed (83°C) for 12 hours. In the morning, the mixture was cooled from 60 to 5°C before filtration. The dark solids were washed with 3x6 liters of cold 25% ethanol to give a light brown product. The wet cake was slurried in 40 liters of water at 30°C for 1 hour and refiltered. The solids were washed well with water and dried at 60°C in air overnight. This gave 10.08 kg, or 10080/77.8 x 170 = 76.3% of the theoretical yield, of the light brown product, 3-(4-pyridinyl)aniline, m.p. 165-167°C.

Claims (3)

1. Fremgangsmåte til fremstilling av 3-(4-pyridinyl)-anilin ved acetylering av 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim for dannelse av det tilsvarende O-acetyloksim og oppvarming av denne forbindelse under sure betingelser, karakterisert ved at man oppvarmer 3-(4-pyridinyl)-2-cykloheksen-1-on-oksim med et overskudd av hver av eddiksyreanhydrid og vannfri fosforsyre, avdestiUerer eddiksyre-biproduktet og overskudd eddiksyreanhydrid, og hydrolyserer det gjenværende N-acetyl-3-(4-pyridinyl)anilin.1. Process for the preparation of 3-(4-pyridinyl)-aniline by acetylating 3-(4-pyridinyl)-2-cyclohexen-1-one oxime to form the corresponding O-acetyl oxime and heating this compound under acidic conditions, characterized by heating 3-(4-pyridinyl)-2-cyclohexen-1-one-oxime with an excess of each of acetic anhydride and anhydrous phosphoric acid, distilling off the acetic acid by-product and excess acetic anhydride, and hydrolyzing the remaining N-acetyl -3-(4-pyridinyl)aniline. 2. Fremgangsmåte ifølge krav 1, karakterisert ved at man anvender ca. 7-10 mol-ekvivalenter eddiksyreanhydrid og ca.3-10 mol-ekvivalenter vannfri fosforsyre pr. mol-ekvivalent oksim.2. Method according to claim 1, characterized in that one uses approx. 7-10 mol-equivalents of acetic anhydride and approx. 3-10 mol-equivalents of anhydrous phosphoric acid per molar equivalent oxime. 3. Fremgangsmåte ifølge krav 2, karakterisert ved at reaktantene i første trinn oppvarmes ved ca. 90-120°C.3. Method according to claim 2, characterized in that the reactants in the first step are heated at approx. 90-120°C.
NO803010A 1979-12-13 1980-10-09 PROCEDURE FOR THE PREPARATION OF 3- (4-PYRIDINYL) ANILIN FROM 3- (4-PYRIDINYL) -2-CYCLOHEXE-1-ON-OXIM. NO803010L (en)

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KR (1) KR830004246A (en)
AR (1) AR225058A1 (en)
AT (1) ATA509880A (en)
AU (1) AU532087B2 (en)
BE (1) BE885570A (en)
CA (1) CA1129864A (en)
DE (1) DE3038778A1 (en)
DK (1) DK432880A (en)
ES (1) ES495606A0 (en)
FI (1) FI803131L (en)
FR (1) FR2471375A1 (en)
GB (1) GB2065635A (en)
IL (1) IL61089A (en)
IT (1) IT1193982B (en)
LU (1) LU82843A1 (en)
NL (1) NL8005661A (en)
NO (1) NO803010L (en)
NZ (1) NZ194952A (en)
PT (1) PT71818B (en)
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US4026900A (en) * 1976-03-19 1977-05-31 Sterling Drug Inc. 3-(Pyridinyl)-2-cyclohexen-1-ones

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PT71818B (en) 1981-07-07
BE885570A (en) 1981-04-08
IL61089A (en) 1983-11-30
LU82843A1 (en) 1981-06-04
IT1193982B (en) 1988-08-31
AU532087B2 (en) 1983-09-15
DK432880A (en) 1981-06-14
ES8107188A1 (en) 1981-09-01
IL61089A0 (en) 1980-11-30
GB2065635A (en) 1981-07-01
SE8007188L (en) 1981-06-14
ES495606A0 (en) 1981-09-01
DE3038778A1 (en) 1981-06-19
NL8005661A (en) 1981-07-16
JPS5687563A (en) 1981-07-16
KR830004246A (en) 1983-07-09
PT71818A (en) 1980-10-01
FR2471375A1 (en) 1981-06-19
AR225058A1 (en) 1982-02-15
ATA509880A (en) 1983-09-15
ZA806200B (en) 1981-09-30
CA1129864A (en) 1982-08-17
FI803131L (en) 1981-06-14
IT8024826A0 (en) 1980-09-22
AU6259480A (en) 1981-06-25
NZ194952A (en) 1982-09-07

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