GB386918A - 1-phenyl-3-methyl-4-alkyl- and -4-aralkyl-pyrazolones and process for the manufacture of same - Google Patents
1-phenyl-3-methyl-4-alkyl- and -4-aralkyl-pyrazolones and process for the manufacture of sameInfo
- Publication number
- GB386918A GB386918A GB24815/32A GB2481532A GB386918A GB 386918 A GB386918 A GB 386918A GB 24815/32 A GB24815/32 A GB 24815/32A GB 2481532 A GB2481532 A GB 2481532A GB 386918 A GB386918 A GB 386918A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- methyl
- under pressure
- methylpyrazolone
- nickel catalyst
- 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
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1-Phenyl-3-methylpyrazolones containing an alkyl, cycloalkyl, or aralkyl residue in the 4-position are prepared by the catalytic hydrogenation under pressure of the corresponding pyrazolones containing an alkylidene, cycloalkylidene or aralkylidene residue. The latter compounds may be hydrogenated simultaneously with their formation by condensation of 1-phenyl-3-methylpyrazolone with aliphatic, alicyclic or aromatic aldehydes or ketones. The products are useful intermediates for the manufacture of pharmaceutical compounds. According to the examples: (1) 1-phenyl-3-methyl-4-isopropylpyrazolone is obtained by treating 1-phenyl-3-methyl-4-isopropylidenepyrazolone with hydrogen under pressure in the presence of a nickel catalyst; (2) 1-phenyl-3-methylpyrazolone is condensed with ethylmethylketone and the resulting 1-phenyl-3-methyl-4-sec-butylidenepyrazolone then hydrogenated under pressure, using a nickel catalyst, to the 4-sec-butyl compound; (3) 1-phenyl-3-methylpyrazolone is dispersed in cyclohexanone and treated with hydrogen under pressure in presence of a nickel catalyst; the product comprises 1 - phenyl - 3 - methyl - 4 - cyclohexylpyrazolone; by replacing the cyclohexanone with acetone, benzaldehyde and isobutylaldehyde, 1-phenyl-3-methylpyrazolones are obtained which contain an isopropyl, benzyl and isobutyl group respectively in the 4-position.ALSO:1-Phenyl-3-methylpyrazolones containing an alkyl, cycloalkyl or aralkyl residue in the 4-position are prepared by the catalytic hydrogenation under pressure of the corresponding pyrazolones containing an alkylidene, cycloalkylidene or aralkylidene residue. The latter compounds may be hydrogenated simultaneously with their formation by condensation of 1-phenyl-3-methylpyrazolone with aliphatic, alicyclic or aromatic aldehydes or ketones. According to the examples, (1) 1-phenyl - 3 - methyl - 4 - isopropylpyrazolone is obtained by treating 1-phenyl-3-methyl-4-isopropylidenepyrazolone with hydrogen under pressure in the presence of a nickel catalyst; (2) 1-phenyl-3-methylpyrazolone is condensed with ethylmethylketone and the resulting 1 - phenyl-3-methyl-4-sec - butylidenepyrazolone then hydrogenated under pressure, using a nickel catalyst, to the 4-sec-butyl compound; (3) 1-phenyl-3-methylpyrazolone is dispersed in cyclohexanone and treated with hydrogen under pressure in presence of a nickel catalyst; the product comprises 1-phenyl-3-methyl-4-cyclohexylpyrazolone; by replacing the cyclohexanone with acetone, benzaldehyde and isobutylaldehyde, 1-phenyl-3-methylpyrazolones are obtained which contain an isopropyl, benzyl and isobutyl group respectively in the 4-position.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE386918X | 1931-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB386918A true GB386918A (en) | 1933-01-26 |
Family
ID=6371047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24815/32A Expired GB386918A (en) | 1931-09-07 | 1932-09-06 | 1-phenyl-3-methyl-4-alkyl- and -4-aralkyl-pyrazolones and process for the manufacture of same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB386918A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000156A (en) * | 1974-06-12 | 1976-12-28 | Agfa-Gevaert N.V. | Preparation of 4-methyl-2-pyrazolin-5-ones |
-
1932
- 1932-09-06 GB GB24815/32A patent/GB386918A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000156A (en) * | 1974-06-12 | 1976-12-28 | Agfa-Gevaert N.V. | Preparation of 4-methyl-2-pyrazolin-5-ones |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2355356A (en) | Preparation of amines | |
| DE515678C (en) | Process for the production of mainly esters among other organic compounds | |
| GB386918A (en) | 1-phenyl-3-methyl-4-alkyl- and -4-aralkyl-pyrazolones and process for the manufacture of same | |
| US2433008A (en) | 4, 6-di-tertiary-butyl-3-methylcyclo-hexanol | |
| GB864926A (en) | Process for preparing novel compounds of the lactone type | |
| US2278372A (en) | Manufacture of amines | |
| GB641662A (en) | Method for making phenol | |
| GB903062A (en) | Dimeric p-isopropenylphenol, a process for its production and its use in the preparation of 1:3:3:trimethyl-1-p-hydroxyphenyl-indan-6-ol | |
| DE956754C (en) | Process for the preparation of cycloaliphatic amines | |
| DE620510C (en) | Process for the preparation of secondary or tertiary amines | |
| DE800400C (en) | Process for the production of oxygen-containing organic compounds | |
| US2052736A (en) | Process for preparing dihydroterpineol and menthone | |
| US1625771A (en) | Manufacture of menthol | |
| DE872342C (en) | Process for the preparation of homologues and analogs of cyclohexanol | |
| US2090319A (en) | Cyclic unsaturated ketones | |
| DE880136C (en) | Process for the production of adipic acid dinitrile | |
| DE493268C (en) | Process for the preparation of inactive menthol | |
| DE961619C (en) | Process for the production of methyl isobutyl ketone | |
| DE874913C (en) | Process for the preparation of aminothiolactones | |
| US1704630A (en) | Manufacture of menthol | |
| DE535254C (en) | Process for the preparation of oxygen-containing organic compounds | |
| DE684797C (en) | Process for the preparation of 1-alkyl-1-arylbutadienes-1,3 from substituted 1-halobutenes-3 | |
| DE1121621B (en) | Process for working up the distillation residues obtained in the production of phenol and acetone by splitting cumene hydroperoxide | |
| DE960199C (en) | Process for the production of cyclohexylhydroxylamine by catalytic hydrogenation of nitrocyclohexane | |
| DE640493C (en) | Process for the production of benzene and toluene |