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
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)
Abstract
The invention relates to the manufacture of 5-pyrazolone derivatives substituted in the 1-position by a group -RXR1NHR11, where R and R1 are residues of the benzene series, R11 is hydrogen or an organic acid radicle, and X is a simple linkage, an oxygen atom, one of the groups -CH : CH-, -CH2-, -NH CO-, or -NHCONH-, or an amino-substituted heterocyclic ring containing carbon and nitrogen, e.g. the residue of a 2 : 5-diamino-1 : 3 : 5-triazine ring, which may be substituted in the 4-position, or the residue of a similarly substituted pyrimidine or quinazoline ring. Such pyrazolones are prepared from amines of the formula NH2RXR1NHR11, where R, R1 and X are as above and R11 is an organic acid radicle, by diazotizing the amines, reducing the diazo compounds to the corresponding hydrazine derivatives, and condensing the latter with esters of b -ketocarboxylic acids. The acid radicle R11 may be split off before or after the production of the pyrazlone, and may afterwards be replaced by another acid radicle. Specified amines for use as starting materials are N-monoacyl derivatives of any of the following compounds: benzidine, tolidine, dianisidine, diphenetidine, 4 : 41-di-aminodiphenyl ether, 4 : 41-diaminostilbene, 4 : 41- or 3 : 31 - diaminodiphenylmethane, 4 : 41-, 4 : 31-, 3 : 41- or 3 : 31-diamonobenzoylaniline, 4 : 41-diaminodiphenylurea, the condensation product from 2 or 3 mols. of m- or p-phenylenediamine and 1 mol. of cyanuric chloride, or the product from 1 mol. of cyanuric chloride, 1 mol. of aniline, and 2 mols. of m- or p-phenylenediamine. Specified esters of b -ketocarboxylic acids are those of formylacetic, acetoacetic, oxalacetic and benzoylacetic acids and aroyldiacetic acids such as terephthaloyldiacetic acid. The products are useful in the manufacture of azo dyes (cf. Specification 486,660). In the examples, (1) monoacetylbenzidine is diazotized, the diazo solution is treated with stannous chloride, and the hydrazine so obtained, or its hydrochloride, is heated with ethyl acetoacetate, ethyl benzoylacetate, or ethyl oxaloacetate; (2) the hydrazine used in example 1 is boiled with aqueous hydrochloric acid, whereby the acetyl group is split off; the product is then condensed with ethyl acetoacetate. Samples have been furnished, under Sect. 2 (5), of pyrazolones prepared as described above from the following components, the specified amino compounds being in each case diazotized and reduced to yield a hydrazine, which is then condensed with the specified ketocarboxylic ester: (1) acetoacetic ester and monoacetyl-4 : 41-diaminodiphenyl ether, with intermediate elimination of the acetyl group; (2) acetoacetic ester and monoacetyl-4 : 41-diaminodiphenyl ether; (3) sodium oxalacetic ester and monoacetyl-4 : 41-diaminodiphenyl ether, with intermediate elimination of the acetyl group; (4) acetoacetic ester and monoacetyl - 4 : 41 - diaminodiphenylmethane, with intermediate elimination of the acetyl group; (5) sodium oxalacetic ester and monoacetyl - 4 : 41 - diaminodiphenylmethane, with intermediate elimination of the acetyl group; (6) acetoacetic ester and monoacetyl benzidine, with intermediate elimination of the acetyl group and subsequent acylation with benzoyl chloride; (7) as for sample 6, except that p-toluenesulphochloride is used for the final acylation; (8) sodium oxalacetic ester and monoacetylbenzidine, with intermediate elimination of the acetyl group and subsequent acylation with the condensation product of 1 mol. of cyanuric chloride and 1 mol. of aniline; (9) as for sample 6, except that terephthaloyl chloride is used for the final acylation; (10) as for sample 6, except that cinnamoyl chloride is used for the final acylation; (11) benzoylacetic ester and monoacetylbenzidine, with intermediate elimination of the acetyl group; (12) terephthaloyldiacetic ester and monoacetylbenzidine, with intermediate elimination of the acetyl group; (13) acetoacetic ester and monoacetyl-o, o1-dichlorobenzidine, with intermediate elimination of the acetyl group; (14) sodium oxalacetic ester and monoacetyl-o, o1-dichlorobenzidine, with intermediate elimination of the acetyl group; (15) acetoacetic ester and monoacetyl-o-tolidine, with intermediate elimination of the acetyl group; (16) sodium oxalacetic ester and monoacetyl-o-tolidine, with intermediate elimination of the acetyl group; (17) acetoacetic ester and monoacetyl-4 : 41-diamino diphenylurea (prepared by condensing p-aminoacetanilide with p-nitrophenylurea chloride and reducing the nitro group in the product); (18) acetoacetic ester and 4-(41-acetylaminobenzoyl)amino-1-aminobenzene-2-sulphonic acid (prepared by condensing p-nitrobenzoyl chloride with p-phenylenediaminesulphonic acid, reducing the nitro group in the product, and treating the diamine so obtained with 1 mol. of acetic anhydride); (19) acetoacetic ester and a monoacetyldiaminodisulphonic acid prepared by condensing 1 mol. of cyanuric chloride with 1 mol. each of monoacetyl-p-phenylenediaminesulphonic acid, p-phenylenediaminesulphonic acid, and aniline. The Specification as open to inspection under Sect. 91 includes an example in which the pyrazolone produced as in example 2 above is acylated by reaction with cyanuric acid, phosgene, or 2 : 3-oxynaphthoic acid chloride. The samples schedule includes a description of the preparation of pyrazolones from (1) sodium oxalacetic ester and monoacetylbenzidine, with intermediate elimination of the acetyl group, subsequent acylation with cyanuric chloride, and a final reaction with aniline, whereby a chlorine atom of the cyanuric residue is replaced by a phenylamino group; the product is identical with sample 8 above; (2) monoacetylbenzidine and acetoacetic ester, with intermediate elimination of the acetyl group and subsequent reaction with 2 : 4-dichlor quinazoline. This subject-matter does not appear in the Specification as accepted.
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 (en) |
NL (1) | NL48318C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3503844A1 (en) * | 1984-02-10 | 1985-08-14 | Sandoz-Patent-GmbH, 7850 Lörrach | Heterocyclic compounds containing basic and/or cationic groups and azo compounds prepared therefrom |
FR2559483A1 (en) * | 1984-02-10 | 1985-08-16 | Sandoz Sa | HETEROCYCLIC COMPOUNDS CONTAINING BASIC AND / OR CATIONIC GROUPS, THEIR PREPARATION AND THEIR USE AS 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 (en) * | 1984-02-10 | 1985-08-14 | Sandoz-Patent-GmbH, 7850 Lörrach | Heterocyclic compounds containing basic and/or cationic groups and azo compounds prepared therefrom |
FR2559483A1 (en) * | 1984-02-10 | 1985-08-16 | Sandoz Sa | HETEROCYCLIC COMPOUNDS CONTAINING BASIC AND / OR CATIONIC GROUPS, THEIR PREPARATION AND THEIR USE AS COLORANTS |
GB2153835A (en) * | 1984-02-10 | 1985-08-29 | Sandoz Ltd | Triazinyl azo dyestuffs and intermediates |
Also Published As
Publication number | Publication date |
---|---|
NL48318C (en) |
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