GB954269A - Process for the production of beta-keto amides - Google Patents
Process for the production of beta-keto amidesInfo
- Publication number
- GB954269A GB954269A GB11863/62A GB1186362A GB954269A GB 954269 A GB954269 A GB 954269A GB 11863/62 A GB11863/62 A GB 11863/62A GB 1186362 A GB1186362 A GB 1186362A GB 954269 A GB954269 A GB 954269A
- Authority
- GB
- United Kingdom
- Prior art keywords
- urethane
- phenyl
- methyl ketone
- naphthyl
- methyl
- 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
- 150000004798 β-ketoamides Chemical class 0.000 title 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 abstract 11
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 8
- NLPHXWGWBKZSJC-UHFFFAOYSA-N 4-acetylbenzonitrile Chemical compound CC(=O)C1=CC=C(C#N)C=C1 NLPHXWGWBKZSJC-UHFFFAOYSA-N 0.000 abstract 4
- YJFNFQHMQJCPRG-UHFFFAOYSA-N 1-(4-ethoxyphenyl)ethanone Chemical compound CCOC1=CC=C(C(C)=O)C=C1 YJFNFQHMQJCPRG-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 3
- -1 alkali-metal alkoxides Chemical class 0.000 abstract 3
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 abstract 2
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 abstract 2
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 abstract 2
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- RDCNKBVMLNCTEV-UHFFFAOYSA-N ethyl n-(3-fluorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=CC(F)=C1 RDCNKBVMLNCTEV-UHFFFAOYSA-N 0.000 abstract 2
- DINDVNWMRYDSGO-UHFFFAOYSA-N ethyl n-(4-fluorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(F)C=C1 DINDVNWMRYDSGO-UHFFFAOYSA-N 0.000 abstract 2
- ARNSTSIXMKZQBC-UHFFFAOYSA-N ethyl n-naphthalen-1-ylcarbamate Chemical compound C1=CC=C2C(NC(=O)OCC)=CC=CC2=C1 ARNSTSIXMKZQBC-UHFFFAOYSA-N 0.000 abstract 2
- RPJQHJLOMYJUHA-UHFFFAOYSA-N ethyl n-pyridin-4-ylcarbamate Chemical compound CCOC(=O)NC1=CC=NC=C1 RPJQHJLOMYJUHA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- DWPLEOPKBWNPQV-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(C)=O DWPLEOPKBWNPQV-UHFFFAOYSA-N 0.000 abstract 1
- ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 abstract 1
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 abstract 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 abstract 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 abstract 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 abstract 1
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 abstract 1
- HSOBVFHPMJPPMD-UHFFFAOYSA-N 3-(2-methoxyphenyl)-3-oxo-n-phenylpropanamide Chemical compound COC1=CC=CC=C1C(=O)CC(=O)NC1=CC=CC=C1 HSOBVFHPMJPPMD-UHFFFAOYSA-N 0.000 abstract 1
- YMLALJWQMVHDEO-UHFFFAOYSA-N 3-(4,7-dimethoxynaphthalen-1-yl)-3-oxo-N-phenylpropanamide Chemical compound COC1=CC=C(C2=CC(=CC=C12)OC)C(=O)CC(=O)NC1=CC=CC=C1 YMLALJWQMVHDEO-UHFFFAOYSA-N 0.000 abstract 1
- XQATXBAZWMESER-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-oxo-n-phenylpropanamide Chemical compound C1=CC(Cl)=CC=C1C(=O)CC(=O)NC1=CC=CC=C1 XQATXBAZWMESER-UHFFFAOYSA-N 0.000 abstract 1
- VPCRKJJHOOWSIM-UHFFFAOYSA-N C(#N)C1=CC=C(NC(CC(C2=CC=CC=C2)=O)=O)C=C1 Chemical compound C(#N)C1=CC=C(NC(CC(C2=CC=CC=C2)=O)=O)C=C1 VPCRKJJHOOWSIM-UHFFFAOYSA-N 0.000 abstract 1
- GDALFUAZKRGAQU-UHFFFAOYSA-N CC(=O)C.C(C)C=1N=C(SC1)CC Chemical compound CC(=O)C.C(C)C=1N=C(SC1)CC GDALFUAZKRGAQU-UHFFFAOYSA-N 0.000 abstract 1
- YPJRVSQKDZEFGS-UHFFFAOYSA-N CC1=C(C(=CC(=C1)C)OCCCC)NC(=O)OCC.CC(=O)C.ClC=1SC=CC1 Chemical compound CC1=C(C(=CC(=C1)C)OCCCC)NC(=O)OCC.CC(=O)C.ClC=1SC=CC1 YPJRVSQKDZEFGS-UHFFFAOYSA-N 0.000 abstract 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 abstract 1
- CJRILLVXZDAQBZ-UHFFFAOYSA-N aniline;lithium Chemical compound [Li].NC1=CC=CC=C1 CJRILLVXZDAQBZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- HKTSLDUAGCAISP-UHFFFAOYSA-N ethyl n,n-diphenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OCC)C1=CC=CC=C1 HKTSLDUAGCAISP-UHFFFAOYSA-N 0.000 abstract 1
- ADHVNWDXMAZGKL-UHFFFAOYSA-N ethyl n-(2,4-dichlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C=C1Cl ADHVNWDXMAZGKL-UHFFFAOYSA-N 0.000 abstract 1
- QVEJMWYRBWYKTO-UHFFFAOYSA-N ethyl n-(4-phenylphenyl)carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C1=CC=CC=C1 QVEJMWYRBWYKTO-UHFFFAOYSA-N 0.000 abstract 1
- BAFPGGUKCVCSKG-UHFFFAOYSA-N ethyl n-[4-chloro-3-(trifluoromethyl)phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 BAFPGGUKCVCSKG-UHFFFAOYSA-N 0.000 abstract 1
- ZSPLIQCHGCWFCS-UHFFFAOYSA-N ethyl n-naphthalen-2-ylcarbamate Chemical compound C1=CC=CC2=CC(NC(=O)OCC)=CC=C21 ZSPLIQCHGCWFCS-UHFFFAOYSA-N 0.000 abstract 1
- YLRSARVOZNPQKX-UHFFFAOYSA-N ethyl n-pyridin-3-ylcarbamate Chemical compound CCOC(=O)NC1=CC=CN=C1 YLRSARVOZNPQKX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- BVPHBAOCFOVKQB-UHFFFAOYSA-N n,4-diphenylbenzamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC1=CC=CC=C1 BVPHBAOCFOVKQB-UHFFFAOYSA-N 0.000 abstract 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 abstract 1
- 101150009274 nhr-1 gene Proteins 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000002221 trityl group Chemical class [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000003673 urethanes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US107035A US3130228A (en) | 1961-05-02 | 1961-05-02 | Process for the production of beta-keto amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB954269A true GB954269A (en) | 1964-04-02 |
Family
ID=22314514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11863/62A Expired GB954269A (en) | 1961-05-02 | 1962-03-28 | Process for the production of beta-keto amides |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3130228A (enrdf_load_stackoverflow) |
| BE (1) | BE616867A (enrdf_load_stackoverflow) |
| CH (1) | CH401026A (enrdf_load_stackoverflow) |
| GB (1) | GB954269A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5124482A (en) * | 1988-02-22 | 1992-06-23 | Warner-Lambert Company | Process for trans-6-(2-substituted-pyrrol-1-yl)alkyl)pyran-2-one inhibitors of cholesterol synthesis |
| CN114249667B (zh) * | 2022-01-11 | 2023-12-26 | 衡阳师范学院 | 一种叔丁醇盐催化的两步一锅反应制备n-h酮酰胺的方法 |
-
0
- BE BE616867D patent/BE616867A/xx unknown
-
1961
- 1961-05-02 US US107035A patent/US3130228A/en not_active Expired - Lifetime
-
1962
- 1962-03-28 GB GB11863/62A patent/GB954269A/en not_active Expired
- 1962-05-01 CH CH519962A patent/CH401026A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH401026A (de) | 1965-10-31 |
| US3130228A (en) | 1964-04-21 |
| BE616867A (enrdf_load_stackoverflow) |
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