DE1543885A1 - Process for the preparation of derivatives of the 5-halo-benzoic acid esters - Google Patents

Process for the preparation of derivatives of the 5-halo-benzoic acid esters

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Publication number
DE1543885A1
DE1543885A1 DE19661543885 DE1543885A DE1543885A1 DE 1543885 A1 DE1543885 A1 DE 1543885A1 DE 19661543885 DE19661543885 DE 19661543885 DE 1543885 A DE1543885 A DE 1543885A DE 1543885 A1 DE1543885 A1 DE 1543885A1
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Prior art keywords
derivatives
denotes
preparation
group
benzoic acid
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DE19661543885
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German (de)
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DE1543885C3 (en
DE1543885B2 (en
Inventor
Akira Morimoto
Hisashi Takosugi
Hideyuki Yoshimitsu
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Societe dEtudes Scientifiques et Industrielles de lIle de France SA
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Societe dEtudes Scientifiques et Industrielles de lIle de France SA
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Publication of DE1543885B2 publication Critical patent/DE1543885B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)

Description

SOCIETE D1ETUDES SCIENTIFIt-iUES ET INDUSTJtI ELLES DE L1ILE-De=PRANCESOCIETE D 1 ETUDES SCIENTIFIt-iUES ET INDUSTJtI ELLES DE L 1 ILE-De = PRANCE

k6 Boulevard de Latour-Maubourg PAHIS 7e, Frankreich k6 Boulevard de Latour-Maubourg PAHIS 7e, France

Verfahren zur Herstellung von Derivaten der 5-Halogen-BenzoeaäureeaterProcess for the preparation of derivatives of the 5-halo-benzoic acid ethers

Vorliegende Erfindung bezieht eich auf ein Verfahren zur Herstellung von Derivaten der 5~Halogen-Benzoesäureeater, welches sich dadurch kennzeichnet, daß man Derivate der 5-Halogen-Benzoeaäure der allgemeinen Formel (i) mit Verbindungen der allgemeinen Formel (Xl) unter Bildung von Derivaten der 5-Halogen-Benzoeaäureeater der allgemeinen Formel (XII.) umsetzt.The present invention relates eich to a process for the preparation of derivatives of the 5-halogen benzoic acid ester, which is characterized in that Derivatives of 5-halo-benzoic acid of the general formula (i) with compounds of the general formula (Xl) under Formation of derivatives of the 5-halo-benzoic acid ethers of the general formula (XII.).

Die erfindungagemäße Reaktion 1st in der folgenden allgemeinen Formal:The reaction according to the invention is as follows general formal:

8AD ORIGINAL 9 09881/1528AD ORIGINAL 9 09881/152

COORgCOORg

(H)(H)

«5«5

(m)(m)

H2 angegeben, in welcherH 2 indicated in which

R^ Alkoxy oder Hydroxy ist,R ^ is alkoxy or hydroxy, R2 Alkanoylanilno, Nitro oder Anino 1st,R 2 Alkanoylanilno, Nitro or Anino 1st, X Halogen 1st,X halogen 1st, R^ Alkyl iden ist,R ^ is alkyl idene,

eines der Symbole R^ und R_ Wasserstoff und da·one of the symbols R ^ and R_ hydrogen and da audaro Halogen oder -SOuRq bedaufcot (wobei Rgaudaro halogen or -SOuRq bedaufcot (where Rg

WasserstoTf oder Alkyl ist), oder dlo kombinierteIs hydrogen or alkyl), or dlo combined Gruppe von H^ und R- tür Mg stehtt Group of H ^ and R- door M g stands t

R^. = Alkyl undR ^. = Alkyl and

R. β Alkoxy let,R. β alkoxy let,

Beispiele der hier erw&bnten Alkoxy^ruppe Nethoxy-, Xthoxy», Propoxy··» Isopropoxy und Radikal·! Beispiele tür dl« Alkanoylanlnogruppe »iod Axetamido-, Propioneiaido-, Butana»ido- und Pentanaaido-Radikal·} Beispiel· ά·τ Alkylgruppe sind Methyl-, Äthyl-, Propylt Inopropyl» und «utyl-RadikaleiExamples of the alkoxy groups mentioned here are ethoxy, xthoxy, propoxy, isopropoxy and radical! Examples door dl "Alkanoylanlnogruppe" iodo Axetamido-, Propioneiaido-, Butana "ido and Pentanaaido radical ·} Example · ά · τ alkyl group are methyl, ethyl, Propylt Inopropyl" and "utyl-Radikalei

909881/1525909881/1525

Beispiele der Alkyl.lden~Gruppo η .inc! Methylen·*, Xthylidon-*« Propyliden t und Butyliden -Rediknie und Hoiapift.ip TiIr tine Halogen·torn sind ChlorP Brore uqw,Examples of the Alkyl.lden ~ Gruppo η .inc! Methylene · * Xthylidon- * t "propylidene and butylidene -Rediknie and Hoiapift.ip tor tine halogen · are torn chlorine P Brore uqw,

Di· Ausgangsstoffe (i) beim erfinduiigegewfincm Vorfahren sind neuartig« Verbindungen. Einige von lhJiBn1 beispielsweise 4-Amino"5-Helogeneelizyieäuret können hergestellt werdenr indem man 3~Amino»tl-Halogenphem>X in Anwesenheit trasaerfreien Kalluukarbonate eit Kohlendiozyd unter erhöhtem Druck in Autoklaven utnectzt. 5"Hal0een~2~Methoxy-4~NitrobenEoesäure kann nan duroh Ueaetzen von 2 Mothyl-^-Halogen-S-Kitroaniaol mit «inori Oxytißtion&mi fiel herstellen .The starting materials (i) in the inventive ancestors are novel compounds. Some of lhJiBn 1, for example, 4-amino "5-Helogeneelizyieäure t may be prepared r by 3 ~ amino"tl-Halogenphem> X in the presence trasaerfreien Kalluukarbonate eit Kohlendiozyd under elevated pressure in an autoclave utnectzt. 5 "Hal0een ~ 2 ~ methoxy-4 Nitrobeneoic acid can be produced by reacting 2 Mothyl - ^ - Halogen-S-Kitroaniaol with inori oxytosis.

Di© anderen Ausgangsstoffe können nbeufulle durcli die gleichen, oben angegebenen Verfahren bereitet- ; tden.The other starting materials can be deflated prepares the same procedures given above; tden.

Die Reaktion beim erfindungcgeniftßen VerfaJirrn durchgerührt, indem man Derivate der J^Haloßenbc säure (l) mit der Vorbindung der allgemeinen Γο (II) umsetzt.The reaction in the process of the invention carried out by taking derivatives of the J ^ Halossebc acid (l) with the prebinding of the general Γο (II) implements.

Die Vorbindungon (Xl) bedeuten Mono (oder O -Alkylenli f i-t , /,Akylhalogenido oder lJiaaoelkaneThe pre-bonds (Xl) mean mono (or O -Alkylenli f i-t, /, Akylhalogenido or lJiaaoelkane

9 0 9 8 8 1/15 2 5 BAD ORIGINAL9 0 9 8 8 1/15 2 5 BAD ORIGINAL

Batapiel« der Mono« (««for Di-) -Alkylaiilfat« sind Mono- (oder Dl-} Methyl«ulfatf !·*··-( od*r Di«) -Xthyleulfat, Mono-(oder Di-) »Butyl««!Tat «mf.fBatapiel "der Mono"("" for Di-) -Alkylaiilfat "are mono- (or Dl-} methyl" sulfate f ! "Butyl""!Tat" mf.f •inige Beiepiela von AlJcylhalef*nid#V tied M*tbyl~ ctilorld ι Äthylbromid, ButylohJU»rid, Prepylbroutid u»V.| einige Beispiele von DiaKöalksiten sind Dlasoaethan, Dlazoäthaa, Dlazopropan uih. 8ο^·να dl· Mono- (oder Dl·) -Alky.lsulfate oder Alky!halogenid· ala Aujagmngmmtottm v©rw*ndet verdöti, ist ec bavorzix^t, die Re afc tion In Anwesenheit eines basis ohne KondensierungeBiittole, wl· Alkalihydroxyd, Erdalkallhydroxyd, Alkalioarbonat, Erdallcal.icArhciriat usw. riurchauilUiren. Die Reaktion kann In Anwesenheit oder Abvoa«nt»it »inoe Lü • Some examples of AlJcylhalef * nid # V tied M * tbyl ~ ctilorld ι ethyl bromide, butyl chloride, prepylbroutide, etc. | some examples of DiaKöalkiten are Dlasoaethan, Dlazoäthaa, Dlazopropan uih. 8ο ^ · να dl · mono (or Dl ·) -Alky.lsulfate or alky! Halide · ala Aujagmngmmtottm v © rw * friend verdöti, ec bavorzix ^ t, the re tion afc In the presence of a base without KondensierungeBiittole, wl · Alkali hydroxide, alkaline earth hydroxide, alkali carbonate, alkaline earth, arhirate, etc. riurchauilUiren. The reaction can be in the presence or absence of "it" inoe Lü

Wenn vlie Reaktion in eine« Le«ung«teit;tol wire!ι ·ο b»et«ht tür dlodue, falle ·· nicht an der tl*n teilalewt, kein· beaotular· BaaohränjcunR, do ca »emUQ d«r Art der Vai-binduii^-in (IX), worden htStimngami ttöl, wi· Azeton, Zither, eromatischer Rohlenvceeemtofft Bieivth^ir&raaeiid uav. vorxugHVfeiee benutat, d.h., Ajceton, Xthar u»v. werde» bei Vexwendun/f τοπ Mono—If vlie reaction in a "Le" ung "teit; tol wire! Ι · ο b" et "ht door dlodue, fall ·· not at the tl * n Teilalewt, no · beaotular · BaaohränjcunR, do ca" emUQ d "r Kind of Vai-binduii ^ -in (IX), been htStimngami ttöl, wi · acetone, zither, eromatic Rohlenvceeemtofft Bieivth ^ ir & raaeiid uav. vorxugHVfeiee benutat, ie, Ajceton, Xthar u »v. will »at Vexwendun / f τοπ Mono— Bi-) -Alkyl8uirat«iü feie Veirbiiiduoeen (il) b»?orarotmaf-lecber Rplijenwaaserstoffr Diu<ethylJTorammitfBi-) -Alkyl8uirat "iü feie Veirbiiiduoeen (il) b"? Orarotmaf-lecber Rplijenwaaserstoff r Diu <ethylJTorammitf

S09P81/1S25S09P81 / 1S25

Einige Beiajileiß der Ηυπο» (i?oUi i;i ) AÄkylaulfat» oind Mono- (oder Di-) MuthyleuliV-ii,.. Mcm«;--(oder Di«) -Äthylsulfat, Mono«(o<ier Di-) -ßufcyleulfai usw.; einige Beispiels von AlkylliöJ-oguniden sind Methyl» chiorid, ÄthyLbroinid, Butylchloridf Propylbrouiid usw.; einige Beispiele von Diazoalkanen oixid Diazomethan, Di&zoäthan, Diassopropan usw. Sofern die Mono« (oder D •Alkylsulfate odsr AlltyJhalogenide als Ausgangsstoffe werden, ißfc eti bevorzugt* die Reaktion in ft aiüefj liAjjiijiiheu Koii;;len3ierving3Kiittelof wie A LI: ■-1 j ί· ;i ilx;:>r,'d ,, üi'.'k« ikalihydro.iiy»31. Aikal isarbonat, Erd a L'.. .·.!.:.f'i.rbfiäiafc a«'; iinrfihauiuhviin, Di.i Raaki;lott l'Some appendices of the Ηυπο "(i? OUi i; i) AÄkylaulfat" oind Mono- (or Di-) MuthyleuliV-ii, .. Mcm "; - (or Di") -Ethylsulfat, Mono "(o <ier Di- ) -sufcyleulfai etc .; oguniden-AlkylliöJ some example of are methyl »chiorid, ÄthyLbroinid, butyl f Propylbrouiid etc .; some examples of diazoalkanes oixid diazomethane, di & zoäthan, Diassopropan etc. If the Mono "(or D • alkylsulphates ODSR AlltyJhalogenide be used as starting materials, ißfc e t i preferably * the reaction in ft aiüefj liAjjiijiiheu koii ;; len3ierving3Kiittelo f as AL I: ■ - 1 j ί ·; i ilx ; :> r, 'd ,, üi'. 'K «ikalihydro.iiy» 3 1. Aikal isarbonat, Erd a L' ... ·.!.:. F'i.rbfiäiafc a «'; iinrfihauiuhviin, Di.i Raaki; lott l'

W'jnn dio ii^akti. -v .! η 3 J na;» J-SdungsmiJ; ϊ^λ .u.iijifiihit, ;lrd: no be ti*1·· oh t i'ü.r diese», fa.lla es nich*. an dar Tiaak '-J >v; toilivUofiH;; k«:Lsi«5 basondsra ßeschrärkun^;, doch ge- ■;.<:[ rt 'ioi- .Vt*. de·/ I--j "bi.ritlungeu (Xi)1 wavloii LösungsuiitvOl .-■;l* :ii?;M| A;;h?·:: --'SOsnatieinher Kohlenwasaex'stofff f ■ iiitSÄhyi.fo.riiäfffiiA .1 uaw. varsu^welfle beixutEtj d.h»s t\s.iiti'<u . •ilhh.x' -,!Tt/. wefi-Son b-^i Vsrwenduiijgf von Mono« v*dfi- »>!-.) Alky) s i} i'■ 5;':ϊλ %ls Vorbindungen (IX)W'jnn dio ii ^ akti. -v.! η 3 Y na; » J-SdungsmiJ; ϊ ^ λ .u.iijifiihit,; lrd: no be ti * 1 ·· oh t i'ü.r these », fa.lla es nich *. an dar Tiaak '-J>v;toilivUofiH;; k «: Lsi« 5 basondsra ßeschrärkun ^ ;, but ge ■;. <: [ r t 'ioi- .Vt *. de · / I - j "bi.ritlungeu (Xi) 1 wavloii LösungsuiitvOl .- ■; l *?: ii M | A ;; h * :: - 'SOsnatieinher Kohlenwasaex'stoff f f ■ iiitSÄhyi.fo .riiäfffiiA .1 uaw. varsu ^ welfle beixutEtj ie " s t \ s.iiti '<u. • ilhh.x' -,! Tt /. wefi-Son b- ^ i Vsrwenduiijgf from Mono« v * dfi- »> ! -.) Alky) si} i '■ 5;': ϊλ% ls prebindings (IX)

909 8 81/1525909 8 81/1525

BAD OF«GlNAt BAD OF «G lNAt

Ufjv/. Eiud hai Vo-n;omli«ng vcm "ilk-lh?;!.>£&*» Ιό ι a äugt Uiid AtIu- "ι"!?, "o.inil iv i-viA-·* ir f. ·*.*= luUu'f-, "v« Dinsjonllr.anen b vorlag·:«Ufjv /. Eiud hai Vo-n; omli «ng vcm"ilk-lh?;!.> £ & * »Ιό ι a eyes Uiid AtIu-" ι "!?," O.inil iv i-viA- · * ir f. · *. * = LuUu'f-, "v" Dinsjonllr.anen b present ·: «

HeI Verwendung der Mono· (mUsT Di-) «Älfcyi j r der AXkyHifc.l«g&«iiia jfiihrt mun <1ίί Reaf;tlon Im all gieln.-m un-iei' Erhitns^n iinri Ilüokfluti * urch. lici V-^rwendunjc ri;?r DiazoalkariS ei'lOiyt die f)^rollführung tm al χ gemeine! η h i i Π»ι;.τ. l- ->jüpo>-.- tu c ■HeI use the mono · ( must Di-) «Älfcyi j r the AXkyHifc.l« g & «iiia jfiihrt mun <1ίί Reaf; tlon In all gieln.-m un-iei 'Erhitns ^ n iinri Ilüokfluti * urch. lici V- ^ rwendunjc ri;? r DiazoalkariS ei'lOiyt the f) ^ roller guide tm al χ common! η h ii Π »ι ; .τ. l - ->jüpo> -.- tu c ■

^vivat^.· eier^ vivat ^. · eggs

.<·· Liiil neu und bei *l^»· Pe »„. «,^ΙΙ-,-ϊγ vou be:I.sr* »..-·'■ .-.v.v. <·· Liiil new and at * l ^ »· Pe» „. «, ^ ΙΙ -, - ϊγ vou be: I.sr *» ..- · '■ .-. V.v

ihü und '.ifihü and '.if

!.»λ·«/!! brauchbari/i.rU?iaaikei ϊ h:· !. »Λ ·« / !! usablei / i.rU? iaaikei ϊ h: ·

Die lOlg der ErfindungThe lOlg of the invention

derthe

ri ,ri,

909881/1525909881/1525

Zu eine χ τ.α.wiig von iro g 4 welche in 1-c «-.ra absoluten Azetons aufgelöst int, werden 1,6 g Kalifir.ike.rbonaci- Anhydrid mit Rühren unter StoO-dimpfuag {dwifjpxoofiiig} hinzugcpotzt und ferner werden 1*5 J? Dieii-uylsnlfift zugegeben. Dae Ooin.ionh wird bei 15 -fttündieein Rühren unter Rückfluß gehalten und dann filtriert. »as Fll^rat wird mit Aktivkohle behandelt und das LPnungsFilttel abdestilliort. Dor KUcI<:afcan<I wird aus v&ssrigeni Methanol uiakri yinllieiort und man erhHlt, l-c»i| q Methyl 2-Methoyy~'f- Λι;ι1ηο 5 Of1.6 g of Kalifir.ike.rbonaci anhydride are added to a χ τ.α.wiig of i r og 4 which is dissolved in 1-c «-.ra absolute acetone with stirring under StoO-dimpfuag {dwifjpxoofiiig} and furthermore 1 * 5 J? Dieii-uylsnlfift added. Dae Ooin.ionh is refluxed at 15 ft. Hour with stirring and then filtered. The filler is treated with activated charcoal and the LPungsFilttel is distilled off. Dor KUcI <: afcan <I is uiakri yinllieiort from v & ssrigi methanol and one obtains, lc »i | q Methyl 2-Methoyy ~ 'f- Λι; ι1ηο 5 Of ale weiße Kristalle :tiit dem Schmelzpunlct 135 bia i3?°C. Ausbeute ■>!. i. All white crystals: with a melting point of 135 to 13 ° C. Yield ■> !. i.

gerechnet auf C„H- O_NC1calculated on C "H- O_NC1

f. 5'»rl?» H htGjf N 6rh9: Cl lCtkk, f. 5 '»rl?» H h t Gjf N 6 r h9: Cl lC t kk,

H f4{64; NH f 4 { 64; N

Beigpiel 2 , * Example 2, *

Zu «ine τ IM au ng -von h,,? {J 2-Methoxy If-Nitro 5~To «ine τ IM au ng -von h ,,? {J 2-methoxy If-nitro 5 ~

3 Chlorbeusot+eüuro in loo cm absoluten Azeton« werden3 Chlorbeusot + euro in 100 cm of absolute acetone ” 3p65 ^ Ktiftimarbonut, Z£*l ons^ DiSiGthyli-ulfat und Io cnr Aceton Uir·: i.f ogoben und daa Gemisch unter Rühren und l6 0tfindlf;< üf lirhitaen bei 65°C unter Rückfluß gehalten.3p65 ^ Ktiftimarbonut, Z £ * l ons ^ DiSiGthyli-ulfat and Io cnr Aceton Uir ·: if ogoben and daa mixture with stirring and 16 0tfindlf; <üf lirhitaen refluxed at 65 ° C.

ο -ο -

90988 1/152590988 1/1525

BADBATH

Nach Vollendung der Reaktion wird dae ReaktionsgeMiaeh filtriert und der zurückbleibend© Kuchen wird mit Aceton gewaschen. Das Piltrat und die Waschflüssigkeit·» werden miteinander vereinigt und das Lösungsmittel abdestilliert. Man erhält 4,91 g Methyl-2 Hethoxr-4-Nitro-5~Chlorbonsoat als farblose, blättrige Kristalle. Die Auebeute betrügt 98,2 #.After the completion of the reaction, the reaction will grow filtered and the remaining cake is washed with acetone washed. The piltrate and the washing liquid are combined with one another and the solvent is distilled off. 4.91 g of methyl 2-methoxy-4-nitro-5-chlorobonsoate are obtained as colorless, leafy crystals. The yield is 98.2 #.

Die Kristalle werden unter Verwendung von ο,5 β tiver Kohle aus einem aus 85 cnr Methanol und 2o cra^ Wasser bestehenden Lttaungeniittolgewisoh undcristalllsiert, wobei stich 4r.5O g der gereinigten Kristalle ale farbloseThe crystals are undcristalllsiert existing Lttaungeniittolgewisoh using ο, 5 β tiver coal from a CNR of 85 methanol and 2o cra ^ water, 4 r engraving .5O g of purified crystals ale colorless

DlHt'ionen bildon. Der Schmelzpunkt beträgt XXk bi· 115,5° C und die Ausbeute belauft'sich auf 91 e 5 56.DlHt'ionen bildon. The melting point is XXk to 115.5 ° C and the yield is 91 e 5 56.

Analyse: berechnet auf CgHgJAnalysis: calculated on CgHgJ

C >f4eol{ H 3,28; N 5#7<M Cl XhtkJ. Gefunden; 0 H'J,835 Ii 3r52; N 5r°l| Cl lh,62. C> f4 e ol {H 3.28; N 5 # 7 <M Cl Xh t kJ. Found; 0 H'J , 835 Ii 3r52; N 5r ° l | Cl lh, 62.

BAD ORIGINALBATH ORIGINAL

90988 1/152590988 1/1525

Claims (1)

PatentanspruchClaim Verfahren sur Herstellung von Derivaten der 5-Halogenbensoesäureeeter, dadurch g e k e η η -seiehnet, daß nan Derivate der 5-Balogenbensoe·Process for the preparation of derivatives of the 5-halobene acid, characterized in that the derivatives of the 5-halobene sfture der allgemeinen Formel»sfture of the general formula » COOHCOOH in welcher R« eine Alkoxy* oder Hydroxygruppe bedeutet, R_ eine Alkanoylamino-, Nitro» oder Aoinogruppe ist und X ein Halogenatom bedeutet, nit einer Verbindung der allgemeinen Formel*in which R «denotes an alkoxy * or hydroxyl group, R_ is an alkanoylamino, nitro or aoino group and X denotes a halogen atom, with a compound of the general formula * in welcher FU eine Alkvlidengruppe bedeutet und R„ ufad Rj1 einerseits ein Vas sera toffatoai und andererseits ein Halogeneto» oder die Gruppe -SO3Rg bedeuten, wobei ein Wasserstoffatom oder eine Alkylgruppe 1st, oderin which FU denotes an Alkvlidengruppe and R "ufad Rj 1 on the one hand a Vas sera toffatoai and on the other hand a Haleto" or the group -SO 3 Rg, where a hydrogen atom or an alkyl group is, or 9098 8 1/15259098 8 1/1525 BADBATH die kombA»;'.'.;·:■ ;:<* ds*;· ^the combA »; '.'.; ·: ■ ; : <* ds *; · ^ U_ Ist» ur>.v..sr Bildung ironU_ is »ur> .v..sr education iron ci»rci »r ltaccording to 0OQB50OQB5 in welcher R^ «in« Alkylgruppe iafe, Jrn,. eins Alkoxygruppe bedeutet und R« «n<3 X die obige Beöaurung haben, aweetat, in which R ^ «in« alkyl group iafe, Jr n,. one denotes an alkoxy group and R «« n <3 X have the above expression , aweetat, 909881/1525909881/1525
DE1543885A 1965-12-10 1966-12-02 Process for the preparation of 2-methoxy ^ -amino-S-chlorobenzoic acid methyl ester Expired DE1543885C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7613165 1965-12-10

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DE1543885A1 true DE1543885A1 (en) 1970-01-02
DE1543885B2 DE1543885B2 (en) 1973-08-02
DE1543885C3 DE1543885C3 (en) 1974-02-28

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DE1543885A Expired DE1543885C3 (en) 1965-12-10 1966-12-02 Process for the preparation of 2-methoxy ^ -amino-S-chlorobenzoic acid methyl ester

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BE (1) BE690476A (en)
BR (1) BR6685258D0 (en)
CH (1) CH486415A (en)
CS (1) CS150934B2 (en)
DE (1) DE1543885C3 (en)
ES (1) ES334733A1 (en)
FI (1) FI48066C (en)
FR (1) FR1504227A (en)
GB (1) GB1159938A (en)
IL (1) IL26947A (en)
NO (1) NO132956C (en)
OA (1) OA02685A (en)

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Publication number Priority date Publication date Assignee Title
CN102311357B (en) * 2011-10-17 2014-01-08 上海安诺芳胺化学品有限公司 Preparation method of 2-hydroxy-4-aminobenzoic acid

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FI48066C (en) 1974-06-10
ES334733A1 (en) 1967-10-16
OA02685A (en) 1970-12-15
NO132956B (en) 1975-11-03
CS150934B2 (en) 1973-09-17
FR1504227A (en) 1967-12-01
GB1159938A (en) 1969-07-30
DE1543885C3 (en) 1974-02-28
NO132956C (en) 1976-02-11
DE1543885B2 (en) 1973-08-02
BE690476A (en) 1967-05-30
BR6685258D0 (en) 1973-12-04
IL26947A (en) 1970-12-24
CH486415A (en) 1970-02-28
FI48066B (en) 1974-02-28

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