SE431870B - Forfarande for framstellning av 6-klor-alfa-metyl-karbazol-2-ettiksyra - Google Patents
Forfarande for framstellning av 6-klor-alfa-metyl-karbazol-2-ettiksyraInfo
- Publication number
- SE431870B SE431870B SE8001617A SE8001617A SE431870B SE 431870 B SE431870 B SE 431870B SE 8001617 A SE8001617 A SE 8001617A SE 8001617 A SE8001617 A SE 8001617A SE 431870 B SE431870 B SE 431870B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- chloro
- formula
- compound
- coor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000005899 aromatization reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- PUXBGTOOZJQSKH-UHFFFAOYSA-N carprofen Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C(O)=O)C)C=C3NC2=C1 PUXBGTOOZJQSKH-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XWJZVIIPTMHYNQ-UHFFFAOYSA-N diethyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-methylpropanedioate Chemical compound N1C2=CC=C(Cl)C=C2C2=C1CC(C(C)(C(=O)OCC)C(=O)OCC)CC2 XWJZVIIPTMHYNQ-UHFFFAOYSA-N 0.000 description 2
- VCWSZWDBRMAJJJ-UHFFFAOYSA-N diethyl 2-(6-chloro-9h-carbazol-2-yl)-2-methylpropanedioate Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)(C(=O)OCC)C(=O)OCC)C=C3NC2=C1 VCWSZWDBRMAJJJ-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YQVZREHUWCCHHX-UHFFFAOYSA-N (4-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=C(Cl)C=C1 YQVZREHUWCCHHX-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WGRWLYZZSRECAS-UHFFFAOYSA-N 2-methyl-2-(3-oxocyclohexyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)C1CCCC(=O)C1 WGRWLYZZSRECAS-UHFFFAOYSA-N 0.000 description 1
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- KPEKBXBXLPRFIW-UHFFFAOYSA-N diethyl 2-methyl-2-(3-oxocyclohexyl)propanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C1CCCC(=O)C1 KPEKBXBXLPRFIW-UHFFFAOYSA-N 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001376 precipitating 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
- 238000000746 purification Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210479A CH637117A5 (de) | 1979-03-02 | 1979-03-02 | Verfahren zur herstellung eines carbazolderivates. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8001617L SE8001617L (sv) | 1980-09-03 |
| SE431870B true SE431870B (sv) | 1984-03-05 |
Family
ID=4225963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8001617A SE431870B (sv) | 1979-03-02 | 1980-02-29 | Forfarande for framstellning av 6-klor-alfa-metyl-karbazol-2-ettiksyra |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4264500A (enExample) |
| JP (1) | JPS603383B2 (enExample) |
| KR (1) | KR840000115B1 (enExample) |
| AT (1) | AT374180B (enExample) |
| CA (1) | CA1128952A (enExample) |
| CH (1) | CH637117A5 (enExample) |
| DK (1) | DK145741C (enExample) |
| ES (1) | ES489119A0 (enExample) |
| GR (1) | GR67216B (enExample) |
| HU (1) | HU178840B (enExample) |
| LU (1) | LU82205A1 (enExample) |
| NL (1) | NL194126C (enExample) |
| NO (1) | NO153134C (enExample) |
| PT (1) | PT70888B (enExample) |
| SE (1) | SE431870B (enExample) |
| YU (1) | YU18580A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0321147U (enExample) * | 1989-07-06 | 1991-03-01 | ||
| US6013808A (en) * | 1998-06-16 | 2000-01-11 | Pfizer Inc. | Method of purifying carbazole ester precursors of 6-chloro-α-methyl-carbazole-2-acetic acid |
| US6268526B1 (en) | 1998-12-16 | 2001-07-31 | Albemarle Corporation | Palladium catalyzed carbonylation process utilizing aromatic substituted alcohols and/or aromatic substituted alkyl halides |
| US9611217B2 (en) | 2015-05-06 | 2017-04-04 | Chemwerth, Inc. | Synthetic processes of carprofen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3896145A (en) * | 1972-07-24 | 1975-07-22 | Hoffmann La Roche | Carbazoles |
| US4158007A (en) * | 1978-08-21 | 1979-06-12 | Hoffmann-La Roche Inc. | Carbazole methyl malonates |
-
1979
- 1979-03-02 CH CH210479A patent/CH637117A5/de not_active IP Right Cessation
-
1980
- 1980-01-16 CA CA343,748A patent/CA1128952A/en not_active Expired
- 1980-01-24 YU YU00185/80A patent/YU18580A/xx unknown
- 1980-02-20 NO NO800458A patent/NO153134C/no unknown
- 1980-02-27 HU HU8080439A patent/HU178840B/hu unknown
- 1980-02-28 LU LU82205A patent/LU82205A1/de unknown
- 1980-02-28 US US06/125,529 patent/US4264500A/en not_active Expired - Lifetime
- 1980-02-29 GR GR61318A patent/GR67216B/el unknown
- 1980-02-29 PT PT70888A patent/PT70888B/pt unknown
- 1980-02-29 AT AT0113880A patent/AT374180B/de not_active IP Right Cessation
- 1980-02-29 KR KR1019800000857A patent/KR840000115B1/ko not_active Expired
- 1980-02-29 DK DK89280A patent/DK145741C/da not_active IP Right Cessation
- 1980-02-29 SE SE8001617A patent/SE431870B/sv not_active IP Right Cessation
- 1980-02-29 JP JP55024199A patent/JPS603383B2/ja not_active Expired
- 1980-02-29 NL NL8001251A patent/NL194126C/nl not_active IP Right Cessation
- 1980-03-01 ES ES489119A patent/ES489119A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| KR830001890A (ko) | 1983-05-19 |
| DK145741B (da) | 1983-02-14 |
| NL194126B (nl) | 2001-03-01 |
| SE8001617L (sv) | 1980-09-03 |
| DK89280A (da) | 1980-09-03 |
| JPS55118461A (en) | 1980-09-11 |
| HU178840B (en) | 1982-07-28 |
| ATA113880A (de) | 1983-08-15 |
| ES8103733A1 (es) | 1981-03-16 |
| AT374180B (de) | 1984-03-26 |
| JPS603383B2 (ja) | 1985-01-28 |
| PT70888B (en) | 1981-06-11 |
| NO153134C (no) | 1986-01-22 |
| LU82205A1 (de) | 1981-09-10 |
| GR67216B (enExample) | 1981-06-24 |
| KR840000115B1 (ko) | 1984-02-16 |
| DK145741C (da) | 1983-08-01 |
| NO153134B (no) | 1985-10-14 |
| ES489119A0 (es) | 1981-03-16 |
| PT70888A (en) | 1980-03-01 |
| NO800458L (no) | 1980-09-03 |
| CA1128952A (en) | 1982-08-03 |
| NL8001251A (nl) | 1980-09-04 |
| YU18580A (en) | 1983-04-30 |
| US4264500A (en) | 1981-04-28 |
| NL194126C (nl) | 2001-07-03 |
| CH637117A5 (de) | 1983-07-15 |
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| Date | Code | Title | Description |
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