HU187137B - Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid - Google Patents
Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid Download PDFInfo
- Publication number
- HU187137B HU187137B HU822013A HU201382A HU187137B HU 187137 B HU187137 B HU 187137B HU 822013 A HU822013 A HU 822013A HU 201382 A HU201382 A HU 201382A HU 187137 B HU187137 B HU 187137B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- acetic acid
- dialkyl
- pyrrole
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 150000002148 esters Chemical class 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- -1 alkyl acetic acid ester Chemical class 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000011149 active material Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- LSWFPSCFMJSJFK-UHFFFAOYSA-N C(C)C1=C(N(C=C1C)C)CC(=O)O Chemical compound C(C)C1=C(N(C=C1C)C)CC(=O)O LSWFPSCFMJSJFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- JYLBSWKLEBNIFH-UHFFFAOYSA-N 2-(1,4-dimethylpyrrol-2-yl)acetic acid Chemical compound CC=1C=C(CC(O)=O)N(C)C=1 JYLBSWKLEBNIFH-UHFFFAOYSA-N 0.000 description 1
- SYYOUHJJSOLSJD-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)acetic acid Chemical compound CN1C=CC=C1CC(O)=O SYYOUHJJSOLSJD-UHFFFAOYSA-N 0.000 description 1
- GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 description 1
- MJVQXPUPLPINBR-UHFFFAOYSA-N 2-(3-ethoxycarbonyl-1,4-dimethylpyrrol-2-yl)acetic acid Chemical compound CCOC(=O)C=1C(C)=CN(C)C=1CC(O)=O MJVQXPUPLPINBR-UHFFFAOYSA-N 0.000 description 1
- REGBKMQHVZERFN-UHFFFAOYSA-N 2-(3-ethoxycarbonyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CCOC(=O)C=1C=CN(C)C=1CC(O)=O REGBKMQHVZERFN-UHFFFAOYSA-N 0.000 description 1
- XZRQFDHOTXQWEW-UHFFFAOYSA-N 2-(3-ethoxycarbonyl-5-ethyl-1,4-dimethylpyrrol-2-yl)acetic acid Chemical compound CCOC(=O)C=1C(C)=C(CC)N(C)C=1CC(O)=O XZRQFDHOTXQWEW-UHFFFAOYSA-N 0.000 description 1
- HEBRCPZDEBYUHT-UHFFFAOYSA-N 2-(3-ethyl-1H-pyrrol-2-yl)acetic acid Chemical compound C(C)C1=C(NC=C1)CC(=O)O HEBRCPZDEBYUHT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010057040 Temperature intolerance Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- PISHKRUMARWBKY-UHFFFAOYSA-N ethyl 2-(1,4-dimethylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC(C)=CN1C PISHKRUMARWBKY-UHFFFAOYSA-N 0.000 description 1
- YWLMDVDPKZKLNL-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1,4-dimethylpyrrole-3-carboxylate Chemical compound CCOC(=O)CC1=C(C(=O)OCC)C(C)=CN1C YWLMDVDPKZKLNL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SEEXPXUCHVGZGU-UHFFFAOYSA-M sodium;2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetate Chemical compound [Na+].C1=C(CC([O-])=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C SEEXPXUCHVGZGU-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
- 229960003414 zomepirac Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU822013A HU187137B (en) | 1982-06-22 | 1982-06-22 | Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid |
| SE8303565A SE454441B (sv) | 1982-06-22 | 1983-06-21 | Forfarande for framstellning av 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-ettiksyraestrar |
| IN422/DEL/83A IN160016B (enrdf_load_stackoverflow) | 1982-06-22 | 1983-06-21 | |
| AT0228383A AT377255B (de) | 1982-06-22 | 1983-06-21 | Verfahren zur herstellung von 1-alkyl- bzw. 1,4-dialkyl-1h-pyrrol-2-essigsaeure-alkylestern |
| FI832262A FI77023C (fi) | 1982-06-22 | 1983-06-21 | Foerfarande foer framstaellning av 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-aettiksyraestrar. |
| CA000430840A CA1188306A (en) | 1982-06-22 | 1983-06-21 | Process for the preparation of 1-alkyl-or 1,4-dialkyl- 1h-pyrrole-2-acetic acid esters |
| ES523478A ES523478A0 (es) | 1982-06-22 | 1983-06-21 | Procedimiento para la preparacion de alquileteres de acido 1-alquil- o 1,4-dialquil-1h--pirrol-2-acetico. |
| DK287183A DK287183A (da) | 1982-06-22 | 1983-06-21 | Fremgangsmaade til fremstilling af 1-alkyl- eller 1,4-dialkyl-1h-pyrrol-2-eddikesyrealkylestere |
| JP58111141A JPS597162A (ja) | 1982-06-22 | 1983-06-22 | １−アルキル−もしくは１，４−ジアルキル−１ｈ−ピロ−ル−２−酢酸エステルの製法 |
| SU833611594A SU1179921A3 (ru) | 1982-06-22 | 1983-06-22 | Способ получени сложных этиловых эфиров 1-метил-или 1,4-диметил-1 @ -пиррол-2-уксусной кислоты |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU822013A HU187137B (en) | 1982-06-22 | 1982-06-22 | Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187137B true HU187137B (en) | 1985-11-28 |
Family
ID=10957298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822013A HU187137B (en) | 1982-06-22 | 1982-06-22 | Process for producing esters of 1-alkyl- orl,4-dialkyl-1h-pyrrol-acetic acid |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS597162A (enrdf_load_stackoverflow) |
| AT (1) | AT377255B (enrdf_load_stackoverflow) |
| CA (1) | CA1188306A (enrdf_load_stackoverflow) |
| DK (1) | DK287183A (enrdf_load_stackoverflow) |
| ES (1) | ES523478A0 (enrdf_load_stackoverflow) |
| FI (1) | FI77023C (enrdf_load_stackoverflow) |
| HU (1) | HU187137B (enrdf_load_stackoverflow) |
| IN (1) | IN160016B (enrdf_load_stackoverflow) |
| SE (1) | SE454441B (enrdf_load_stackoverflow) |
| SU (1) | SU1179921A3 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987002662A2 (en) * | 1985-10-25 | 1987-05-07 | Sandoz Ag | Heterocyclic analogs of mevalonolactone and derivatives thereof, processes for their production and their use as pharmaceuticals |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
-
1982
- 1982-06-22 HU HU822013A patent/HU187137B/hu not_active IP Right Cessation
-
1983
- 1983-06-21 FI FI832262A patent/FI77023C/fi not_active IP Right Cessation
- 1983-06-21 ES ES523478A patent/ES523478A0/es active Granted
- 1983-06-21 CA CA000430840A patent/CA1188306A/en not_active Expired
- 1983-06-21 AT AT0228383A patent/AT377255B/de not_active IP Right Cessation
- 1983-06-21 IN IN422/DEL/83A patent/IN160016B/en unknown
- 1983-06-21 DK DK287183A patent/DK287183A/da not_active Application Discontinuation
- 1983-06-21 SE SE8303565A patent/SE454441B/sv not_active IP Right Cessation
- 1983-06-22 SU SU833611594A patent/SU1179921A3/ru active
- 1983-06-22 JP JP58111141A patent/JPS597162A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS597162A (ja) | 1984-01-14 |
| FI77023B (fi) | 1988-09-30 |
| SU1179921A3 (ru) | 1985-09-15 |
| SE8303565D0 (sv) | 1983-06-21 |
| ES8500227A1 (es) | 1984-10-01 |
| IN160016B (enrdf_load_stackoverflow) | 1987-06-20 |
| DK287183A (da) | 1983-12-23 |
| FI77023C (fi) | 1989-01-10 |
| FI832262L (fi) | 1983-12-23 |
| JPH0136825B2 (enrdf_load_stackoverflow) | 1989-08-02 |
| AT377255B (de) | 1985-02-25 |
| ATA228383A (de) | 1984-07-15 |
| ES523478A0 (es) | 1984-10-01 |
| DK287183D0 (da) | 1983-06-21 |
| FI832262A0 (fi) | 1983-06-21 |
| SE8303565L (sv) | 1983-12-23 |
| CA1188306A (en) | 1985-06-04 |
| SE454441B (sv) | 1988-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |