GB779703A - Pyrazolone compounds and a process for making them - Google Patents
Pyrazolone compounds and a process for making themInfo
- Publication number
- GB779703A GB779703A GB19796/54A GB1979654A GB779703A GB 779703 A GB779703 A GB 779703A GB 19796/54 A GB19796/54 A GB 19796/54A GB 1979654 A GB1979654 A GB 1979654A GB 779703 A GB779703 A GB 779703A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- acid
- methyl
- group
- hydrogen
- 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
Classifications
-
- 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
- C07D231/38—Nitrogen atoms
Abstract
The invention comprises pyrazolones of the formula: <FORM:0779703/IV(b)/1> where R is benzyl or nuclear-substituted benzyl, R1 is hydrogen or C1-C4 alkyl and R2 and R3 are C1-C4 alkyl or aralkyl. These are prepared from the corresponding pyrazolones without the 4-substituent by treatment with nitrous acid to introduce a 4-nitroso group, reduction to 4-amino and reaction with an aliphatic or aromatic aldehyde in the presence of a reducing agent. Reduction of the nitroso group may be effected by zinc and acid, hydrogen and a Group 8 catalyst, or sodium bisulphite; the latter gives a sulphamic acid which is subsequently hydrolysed. The groups R2 and R3 may be introduced successively with two different aldehydes or simultaneously with two mols. of the same aldehyde. The reducing agent for this step may be formic acid, zinc and acid, or hydrogen and a catalyst. The two reduction steps may be carried out in one process the aldehyde being added at the beginning. Instead of the 4-nitroso group there may be used compounds containing a 4-nitro-, 4-halo, 4-alkylideneamino or 4-aralkylideneamino substituent. Examples show the preparation of products and intermediates where R is benzyl, p-methylbenzyl or o-methoxybenzyl, R1 is methyl or n-propyl and R2, R3 are dimethyl, diethyl, methylisobutyl or methyl-benzyl. In general the benzyl group may be substituted by halogen, lower alkyl or lower alkoxy. 1-Benzyl - 2 - methyl - 3 - n - propyl - 5 - pyrazolone is obtained by heating benzylhydrazine with ethyl butyrylacetate and alkylating the product with methyl iodide. 1-(o-Methoxybenzyl)-2 : 3 - dimethyl - 5 - pyrazolone is obtained similarly.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE779703X | 1953-07-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB779703A true GB779703A (en) | 1957-07-24 |
Family
ID=6687251
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19796/54A Expired GB779703A (en) | 1953-07-06 | 1954-07-06 | Pyrazolone compounds and a process for making them |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB779703A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3978077A (en) * | 1973-04-17 | 1976-08-31 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4000294A (en) | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4002641A (en) | 1973-12-20 | 1977-01-11 | Bayer Aktiengesellschaft | Pyrazole derivatives |
US4005215A (en) | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4045571A (en) | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4053621A (en) | 1974-06-06 | 1977-10-11 | Bayer Aktiengesellschaft | 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them |
US4056533A (en) | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
US4069334A (en) | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
US4081596A (en) | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
-
1954
- 1954-07-06 GB GB19796/54A patent/GB779703A/en not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4061653A (en) * | 1972-06-23 | 1977-12-06 | Bayer Aktiengesellschaft | 1-Substituted-3-amino-pyrazol-5-ones |
US3978077A (en) * | 1973-04-17 | 1976-08-31 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4000294A (en) | 1973-04-17 | 1976-12-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4005215A (en) | 1973-04-17 | 1977-01-25 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4045571A (en) | 1973-04-17 | 1977-08-30 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4056533A (en) | 1973-04-17 | 1977-11-01 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4081596A (en) | 1973-04-17 | 1978-03-28 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4288446A (en) * | 1973-04-17 | 1981-09-08 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
US4002641A (en) | 1973-12-20 | 1977-01-11 | Bayer Aktiengesellschaft | Pyrazole derivatives |
US4069334A (en) | 1973-12-20 | 1978-01-17 | Bayer Aktiengesellschaft | Pyrazole derivatives |
US4053621A (en) | 1974-06-06 | 1977-10-11 | Bayer Aktiengesellschaft | 1-[2-(βNaphthyloxy)ethyl]-3-methylpyrazolone-(5) and antithrombotic and antithrombolytic compositions and methods utilizing them |
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