DE2609835C3 - Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden - Google Patents
Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamidenInfo
- Publication number
- DE2609835C3 DE2609835C3 DE2609835A DE2609835A DE2609835C3 DE 2609835 C3 DE2609835 C3 DE 2609835C3 DE 2609835 A DE2609835 A DE 2609835A DE 2609835 A DE2609835 A DE 2609835A DE 2609835 C3 DE2609835 C3 DE 2609835C3
- Authority
- DE
- Germany
- Prior art keywords
- approx
- hydrogenation
- promoter
- radicals
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 235000021317 phosphate Nutrition 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
- 229910000073 phosphorus hydride Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- WWROGCAUSKGAMX-UHFFFAOYSA-N n-(4-ethoxyphenyl)-3-oxobutanamide Chemical compound CCOC1=CC=C(NC(=O)CC(C)=O)C=C1 WWROGCAUSKGAMX-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- -1 unsaturated heterocyclic amines Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- MARUKTRRDHIKNY-UHFFFAOYSA-N 3-hydroxy-n-phenylbutanamide Chemical compound CC(O)CC(=O)NC1=CC=CC=C1 MARUKTRRDHIKNY-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- PXHVJJICTQNCMI-OUBTZVSYSA-N nickel-60 atom Chemical compound [60Ni] PXHVJJICTQNCMI-OUBTZVSYSA-N 0.000 description 1
- QCYXGORGJYUYMT-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QCYXGORGJYUYMT-UHFFFAOYSA-N 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609835A DE2609835C3 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden |
| CH281777A CH626326A5 (enExample) | 1976-03-10 | 1977-03-07 | |
| JP2450377A JPS52108935A (en) | 1976-03-10 | 1977-03-08 | Preparation of 33hydroxybutyric acid arylamide |
| US05/775,461 US4128578A (en) | 1976-03-10 | 1977-03-08 | Process for the manufacture of 3-hydroxybutyric acid arylamides with trialkyl phosphate and substituted phosphine promotor |
| GB9993/77A GB1535009A (en) | 1976-03-10 | 1977-03-09 | Process for the manufacture of 3-hydroxybutyric acid arylamides |
| FR7707084A FR2343720A1 (fr) | 1976-03-10 | 1977-03-10 | Procede de preparation d'arylamides de l'acide hydroxy-3 butyrique |
| BE175692A BE852340A (fr) | 1976-03-10 | 1977-03-10 | Procede de preparation d'arylamides de l'acide hydroxy-3 butyrique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2609835A DE2609835C3 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2609835A1 DE2609835A1 (de) | 1977-09-22 |
| DE2609835B2 DE2609835B2 (de) | 1978-10-19 |
| DE2609835C3 true DE2609835C3 (de) | 1979-06-07 |
Family
ID=5971961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2609835A Expired DE2609835C3 (de) | 1976-03-10 | 1976-03-10 | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4128578A (enExample) |
| JP (1) | JPS52108935A (enExample) |
| BE (1) | BE852340A (enExample) |
| CH (1) | CH626326A5 (enExample) |
| DE (1) | DE2609835C3 (enExample) |
| FR (1) | FR2343720A1 (enExample) |
| GB (1) | GB1535009A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2837022A1 (de) * | 1978-08-24 | 1980-03-06 | Hoechst Ag | Verfahren zur hydrierung organischer verbindungen |
| DE3003254A1 (de) * | 1980-01-30 | 1981-08-20 | Hoechst Ag, 6000 Frankfurt | Verfahren zur katalytischen hydrierung organischer verbindungen |
| US4689431A (en) * | 1985-02-21 | 1987-08-25 | Japan As Represented By General Director Of Agency Of Industrial Science And Technology | Method for the preparation of phenyl pyruvic acid |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830087A (en) * | 1955-02-21 | 1958-04-08 | Hoechst Ag | beta-hydroxybutyric acid para-phenetidide and a process for preparing it |
| US3051618A (en) * | 1956-11-06 | 1962-08-28 | Hoechst Ag | Beta-hydroxy-butyric acid amide derivatives and process for their use as narcotics |
| BE615636A (enExample) * | 1961-03-29 | 1900-01-01 | ||
| GB1200233A (en) * | 1967-12-21 | 1970-07-29 | British Petroleum Co | Improvements relating to the preparation of hydrogenation catalysts |
| US3737459A (en) * | 1970-08-12 | 1973-06-05 | Union Oil Co | Catalyzed reaction of an arylamine with an alkylamine to form an n-alkyl substituted arylamine |
| US3819734A (en) * | 1972-05-05 | 1974-06-25 | Goodyear Tire & Rubber | Hydrogenation process |
| US3992323A (en) * | 1973-03-26 | 1976-11-16 | Atlantic Richfield Company | Olefin polymerization catalyst |
| DE2435818C3 (de) * | 1974-07-25 | 1982-02-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung aromatischer Diamine |
-
1976
- 1976-03-10 DE DE2609835A patent/DE2609835C3/de not_active Expired
-
1977
- 1977-03-07 CH CH281777A patent/CH626326A5/de not_active IP Right Cessation
- 1977-03-08 US US05/775,461 patent/US4128578A/en not_active Expired - Lifetime
- 1977-03-08 JP JP2450377A patent/JPS52108935A/ja active Granted
- 1977-03-09 GB GB9993/77A patent/GB1535009A/en not_active Expired
- 1977-03-10 BE BE175692A patent/BE852340A/xx not_active IP Right Cessation
- 1977-03-10 FR FR7707084A patent/FR2343720A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH626326A5 (enExample) | 1981-11-13 |
| FR2343720A1 (fr) | 1977-10-07 |
| DE2609835B2 (de) | 1978-10-19 |
| BE852340A (fr) | 1977-09-12 |
| GB1535009A (en) | 1978-12-06 |
| US4128578A (en) | 1978-12-05 |
| DE2609835A1 (de) | 1977-09-22 |
| JPS622582B2 (enExample) | 1987-01-20 |
| FR2343720B1 (enExample) | 1983-09-02 |
| JPS52108935A (en) | 1977-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2609835C3 (de) | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden | |
| DE1248669B (de) | Verfahren zur Herstellung von 2 3-Dihydrofuranen | |
| DE2447824A1 (de) | Herstellung von c tief 1 -c tief 7 aliphatischen hydrocarbylestern von n- eckige klammer auf 2,6-di(c tief 1 -c tief 7 -alkyl)phenyl eckige klammer zu alpha-aminocarbonsaeuren | |
| DE1237567B (de) | Verfahren zur Herstellung von delta 5-6-Methylsteroiden | |
| DE3325983C2 (enExample) | ||
| EP0854856B1 (de) | Verfahren zur reduktion von nitroverbindungen | |
| EP0089417A1 (de) | Verfahren zur Herstellung von Phthalid | |
| DE1272922B (de) | Verfahren zur Herstellung von 2-Alkylcyclopentan-1, 3-dionen | |
| DE1593289B2 (de) | Katalytisches Verfahren zum Hydrieren von aromatischen Verbindungen | |
| EP0142070B1 (de) | Verfahren zur Herstellung von N-Methylhomoveratrylamin | |
| DE1493746B2 (de) | 2- (p-Aminobenzoyloxy)-3-methylnaphtho-l,4-hydrochinon und Verfahren zu seiner Herstellung | |
| DE3137091C2 (de) | Verfahren zur Herstellung von 4-Aminomethyl-benzoesäure aus 4-Hydroxyiminomethyl-benzoesäure | |
| DE828244C (de) | Verfahren zur Hydrierung von ª‡, ª‰-ungesaettigten Ketonen | |
| EP0691331B1 (de) | Verfahren zur Herstellung N-acylierter 2-Chlor-5-aminomethylpyridine | |
| DE683908C (de) | Verfahren zur Herstellung von Trimethylhydrochinon | |
| DE2014837A1 (de) | Verfahren zur Herstellung von Piperidin | |
| DE563767C (de) | Verfahren zur Herstellung von Amidinen | |
| DE862016C (de) | Verfahren zur Herstellung von Tetrahydropyranderivaten | |
| DE2354224C3 (de) | Verfahren zur Herstellung eines Aminobenzolderivats | |
| DE1152388B (de) | Verfahren zur Herstellung oder Wiederherstellung von Katalysatoren unter Verwendung verbrauchter Metalloxyd-Traegerkatalysatoren | |
| DE634275C (de) | Verfahren zur Darstellung von N-Arylglukaminen | |
| AT70874B (de) | Verfahren zur Darstellung von Salzen des Betains. | |
| DE633983C (de) | Verfahren zur Herstellung von Aminoalkoholen quaternaerer aromatisch-aliphatischer Ammoniumbasen | |
| DE2111606A1 (de) | Verfahren zur Herstellung eines Diastereoisomerengemisches aus Zearalanol | |
| DE2343959C3 (de) | Verfahren zur Herstellung von 5-Chlor-2,4-dimethoxyaniIin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |