SE434512B - Forfarande for framstellning av 4-aroyl-substituerade fenoxiettiksyror - Google Patents

Forfarande for framstellning av 4-aroyl-substituerade fenoxiettiksyror

Info

Publication number: SE434512B
Authority: SE; Sweden
Prior art keywords: process according; oxime; dichloro; lower alkyl; reaction
Prior art date: 1979-07-23

Application number

SE8005205A

Other languages

English (en)

Swedish (sv)

Other versions

SE8005205L (sv

Inventor

R L Walters

W R Heitmann

Original Assignee

Abbott Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-07-23

Filing date

1980-07-16

Publication date

1984-07-30

1980-07-16 Application filed by Abbott Lab filed Critical Abbott Lab

1981-01-24 Publication of SE8005205L publication Critical patent/SE8005205L/xx

1984-07-30 Publication of SE434512B publication Critical patent/SE434512B/sv

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims 3
239000002253 acid Substances 0.000 title description 3
150000007513 acids Chemical class 0.000 title 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
150000002923 oximes Chemical class 0.000 claims description 12
-1 alkali metal cation Chemical class 0.000 claims description 9
229910052700 potassium Inorganic materials 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical group CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
239000012429 reaction media Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical group C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims description 2
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 2
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 2
239000002934 diuretic Substances 0.000 claims description 2
229940116269 uric acid Drugs 0.000 claims description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
229940030606 diuretics Drugs 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
238000005580 one pot reaction Methods 0.000 claims 1
230000003248 secreting effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 6
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000047 product Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VEUVOSMVGJHLBK-UHFFFAOYSA-N (2,3-dichloro-4-hydroxyphenyl)-(2-nitrophenyl)methanone Chemical compound ClC1=C(Cl)C(O)=CC=C1C(=O)C1=CC=CC=C1[N+]([O-])=O VEUVOSMVGJHLBK-UHFFFAOYSA-N 0.000 description 1
VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 1
FPSKUEZDUDXRDJ-UHFFFAOYSA-N 2-[2,3-dichloro-4-(4-nitrobenzoyl)phenoxy]acetic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 FPSKUEZDUDXRDJ-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
DBXMLOKHOPZDEN-UHFFFAOYSA-N C(C)=NO.[K] Chemical compound C(C)=NO.[K] DBXMLOKHOPZDEN-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
238000013021 overheating Methods 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SE8005205A 1979-07-23 1980-07-16 Forfarande for framstellning av 4-aroyl-substituerade fenoxiettiksyror SE434512B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/059,823 US4220801A (en)	1979-07-23	1979-07-23	Process for making 4-aroyl-substituted phenoxyacetic acids

Publications (2)

Publication Number	Publication Date
SE8005205L SE8005205L (sv)	1981-01-24
SE434512B true SE434512B (sv)	1984-07-30

Family

ID=22025500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8005205A SE434512B (sv)	1979-07-23	1980-07-16	Forfarande for framstellning av 4-aroyl-substituerade fenoxiettiksyror

Country Status (17)

Country	Link
US (1)	US4220801A (fr)
JP (1)	JPS5620543A (fr)
AU (1)	AU534570B2 (fr)
BE (1)	BE884414A (fr)
CA (1)	CA1137997A (fr)
CH (1)	CH644344A5 (fr)
DE (1)	DE3027765A1 (fr)
ES (1)	ES493563A0 (fr)
FR (1)	FR2461694A1 (fr)
GB (1)	GB2055817A (fr)
GR (1)	GR69715B (fr)
IT (1)	IT1132221B (fr)
NL (1)	NL8004211A (fr)
NZ (1)	NZ194269A (fr)
PH (1)	PH15325A (fr)
SE (1)	SE434512B (fr)
ZA (1)	ZA804134B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR75464B (fr) *	1981-04-24	1984-07-20	Ciba Geigy

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4069344A (en) *	1972-05-10	1978-01-17	Ciba-Geigy Corporation	Insecticidal substituted phenyl derivatives
JPS5195049A (en) *	1975-02-12	1976-08-20		* ********so*notsu***************************************nino
US4058559A (en) *	1975-09-24	1977-11-15	Abbott Laboratories	4-Aroyl-substituted phenoxy acetic acids

1979
- 1979-07-23 US US06/059,823 patent/US4220801A/en not_active Expired - Lifetime
1980
- 1980-07-03 CA CA000355311A patent/CA1137997A/fr not_active Expired
- 1980-07-08 NZ NZ194269A patent/NZ194269A/xx unknown
- 1980-07-08 GB GB8022301A patent/GB2055817A/en not_active Withdrawn
- 1980-07-09 PH PH24259A patent/PH15325A/en unknown
- 1980-07-09 ZA ZA00804134A patent/ZA804134B/xx unknown
- 1980-07-11 AU AU60344/80A patent/AU534570B2/en not_active Ceased
- 1980-07-16 SE SE8005205A patent/SE434512B/sv unknown
- 1980-07-19 GR GR62504A patent/GR69715B/el unknown
- 1980-07-21 ES ES493563A patent/ES493563A0/es active Granted
- 1980-07-22 CH CH560080A patent/CH644344A5/fr not_active IP Right Cessation
- 1980-07-22 DE DE19803027765 patent/DE3027765A1/de not_active Withdrawn
- 1980-07-22 NL NL8004211A patent/NL8004211A/nl not_active Application Discontinuation
- 1980-07-22 IT IT23618/80A patent/IT1132221B/it active
- 1980-07-22 FR FR8016152A patent/FR2461694A1/fr active Granted
- 1980-07-22 BE BE0/201481A patent/BE884414A/fr not_active IP Right Cessation
- 1980-07-22 JP JP9945080A patent/JPS5620543A/ja active Pending

Also Published As

Publication number	Publication date
AU6034480A (en)	1981-01-29
PH15325A (en)	1982-11-24
GB2055817A (en)	1981-03-11
JPS5620543A (en)	1981-02-26
NL8004211A (nl)	1981-01-27
ES8106691A1 (es)	1981-09-01
FR2461694A1 (fr)	1981-02-06
CA1137997A (fr)	1982-12-21
IT1132221B (it)	1986-06-25
CH644344A5 (fr)	1984-07-31
DE3027765A1 (de)	1981-02-19
FR2461694B1 (fr)	1983-04-01
IT8023618A0 (it)	1980-07-22
ES493563A0 (es)	1981-09-01
GR69715B (fr)	1982-07-09
BE884414A (fr)	1981-01-22
US4220801A (en)	1980-09-02
NZ194269A (en)	1982-05-25
SE8005205L (sv)	1981-01-24
AU534570B2 (en)	1984-02-09
ZA804134B (en)	1981-07-29

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IE43142B1 (en)	1980-12-31	Phenylacetic acid derivatives
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SE434512B (sv)	1984-07-30	Forfarande for framstellning av 4-aroyl-substituerade fenoxiettiksyror
SU764608A3 (ru)	1980-09-15	Способ получени фторированных производных алкановых кислот или их солей или их оптически активных изомеров
KR870000205B1 (ko)	1987-02-16	페녹시 알칸디온 유도체의 제조방법
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US3642882A (en)	1972-02-15	Process for the production of nitroarylethermonocarboxylic acids and their esters
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US5723658A (en)	1998-03-03	Process for the preparation of salts of substituted or unsubstituted phthalic acids
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US4504671A (en)	1985-03-12	Method for preparing aldoxime or ketoxime-O-alkanoic acid
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