GB486747A - Manufacture of pyrazolone derivatives - Google Patents
Manufacture of pyrazolone derivativesInfo
- Publication number
- GB486747A GB486747A GB8270/38A GB827038A GB486747A GB 486747 A GB486747 A GB 486747A GB 8270/38 A GB8270/38 A GB 8270/38A GB 827038 A GB827038 A GB 827038A GB 486747 A GB486747 A GB 486747A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetyl group
- ester
- monoacetyl
- acid
- chloride
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 title 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 15
- 230000008030 elimination Effects 0.000 abstract 14
- 238000003379 elimination reaction Methods 0.000 abstract 14
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 12
- 239000002253 acid Substances 0.000 abstract 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 8
- DZQXBXZZSKPMDV-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(N)C=C1 DZQXBXZZSKPMDV-UHFFFAOYSA-N 0.000 abstract 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 6
- 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 abstract 6
- 230000010933 acylation Effects 0.000 abstract 6
- 238000005917 acylation reaction Methods 0.000 abstract 6
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- 239000011734 sodium Substances 0.000 abstract 6
- 229910052708 sodium Inorganic materials 0.000 abstract 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 150000007524 organic acids Chemical group 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- YPRXLILHVBUERT-UHFFFAOYSA-N (4-nitrophenyl)urea hydrochloride Chemical compound C1=CC(=CC=C1NC(=O)N)[N+](=O)[O-].Cl YPRXLILHVBUERT-UHFFFAOYSA-N 0.000 abstract 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 abstract 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 abstract 1
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 abstract 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical group O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 abstract 1
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 abstract 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical class OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 abstract 1
- RRJVSWHPJLGNPA-UHFFFAOYSA-N 4-ethoxy-2,4-dioxobutanoic acid Chemical compound CCOC(=O)CC(=O)C(O)=O RRJVSWHPJLGNPA-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical class 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH486747X | 1935-11-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB486747A true GB486747A (en) | 1938-06-07 |
Family
ID=4516476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8270/38A Expired GB486747A (en) | 1935-11-06 | 1936-11-06 | Manufacture of pyrazolone derivatives |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB486747A (enrdf_load_stackoverflow) |
NL (1) | NL48318C (enrdf_load_stackoverflow) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3503844A1 (de) * | 1984-02-10 | 1985-08-14 | Sandoz-Patent-GmbH, 7850 Lörrach | Basische und/oder kationische gruppen enthaltende heterocyclische verbindungen und daraus hergestellte azoverbindungen |
FR2559483A1 (fr) * | 1984-02-10 | 1985-08-16 | Sandoz Sa | Composes heterocycliques contenant des groupes basiques et/ou cationiques, leur preparation et leur utilisation comme colorants |
-
0
- NL NL48318D patent/NL48318C/xx active
-
1936
- 1936-11-06 GB GB8270/38A patent/GB486747A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3503844A1 (de) * | 1984-02-10 | 1985-08-14 | Sandoz-Patent-GmbH, 7850 Lörrach | Basische und/oder kationische gruppen enthaltende heterocyclische verbindungen und daraus hergestellte azoverbindungen |
FR2559483A1 (fr) * | 1984-02-10 | 1985-08-16 | Sandoz Sa | Composes heterocycliques contenant des groupes basiques et/ou cationiques, leur preparation et leur utilisation comme colorants |
GB2153835A (en) * | 1984-02-10 | 1985-08-29 | Sandoz Ltd | Triazinyl azo dyestuffs and intermediates |
Also Published As
Publication number | Publication date |
---|---|
NL48318C (enrdf_load_stackoverflow) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69225500T2 (de) | Chinazolinone als mittel gegen angina | |
DE69926154T2 (de) | Pyridin-3-carbonsäurederivate und ihre Verwendung als Zwischenprodukte | |
Falco et al. | 2, 4-Diaminopyrimidines as Antimalarials. I. 1 5-Aryloxyl and 5-Alkoxyl Derivatives | |
Shaw et al. | iso Oxazolones. Part VI. The hydrogenation of 5-amino iso oxazoles. A new synthesis of pyrimidines | |
GB486747A (en) | Manufacture of pyrazolone derivatives | |
KR101919097B1 (ko) | 엘트롬보패그의 제조방법 | |
BR0212812A (pt) | Processos para a fabricação de pirazóis substituìdos e composição farmacêutica compreendendo os mesmos | |
GB779703A (en) | Pyrazolone compounds and a process for making them | |
US2759949A (en) | J-amino-x-cyanopyrazole and method | |
Potts | 1: 2: 4-Triazoles. Part I. A synthesis of 3: 5-disubstituted 1: 2: 4-triazoles | |
Baker et al. | Analogs of tetrahydrofolic acid VII. Synthesis of N‐[1‐(2‐amino‐4‐hydroxy‐6‐methyl‐5‐pyrimidyl)‐3‐propyl]‐p‐aminobenzoyl‐L‐glutamic acid, an inhibitor of folic reductase | |
US3163646A (en) | J-aminobenzotriazinones- | |
US2694714A (en) | Fast bases of the quinoline series | |
US2637732A (en) | Process for the manufacture of | |
US1534512A (en) | 1-aryl-5-pyrazolones and process of making same | |
Koelsch | An Indole Synthesis from a m-Carboxyphenylhydrazone | |
Nisbet et al. | 206. Heterocyclic ketones. Part I. β-Amino-ketones and related pyrazolines derived from benzylidene-and furfurylidene-acetone | |
DE892817C (de) | Verfahren zur Herstellung weissgegerbter Leder | |
Hassan et al. | Synthesis and biological evaluation of schiff bases and pyrazole derivatives derive from chalcones,(2e)-1-(4-Aminophenyl)-3-(2-Furyl) Prop-2-En-1-one | |
GB632832A (en) | Manufacture of pyrazolones substituted in the 3-position | |
Tsuda et al. | Communications-The Total Synthesis of Nordehydro-α-matrinidine (4, 5, 6, 8, 9, 10-Hexahydropyrido [3, 4, 5i, j] quinolizine) | |
DE904410C (de) | Verfahren zur Herstellung von 1-Acylaminoaryl-5-pyrazolonen | |
DE833811C (de) | Verfahren zur Herstellung von Abkoemmlingen von Sulfonamiden der aromatischen Reihe | |
Vaughan | 2, 3-PYRROLIDINEDIONES. VI. REACTIONS WITH PHENYLHYDRAZINE | |
GB907758A (en) | Diazo dyes derived from benzoylaminosulphonic acids and their use in silver-dye bleach processes |