CA1108628A - Production of pyrrolidin-2-ones from 2-pyrrolin-2- ones and the production of 3-pyrrolin-2-ones - Google Patents
Production of pyrrolidin-2-ones from 2-pyrrolin-2- ones and the production of 3-pyrrolin-2-onesInfo
- Publication number
- CA1108628A CA1108628A CA329,322A CA329322A CA1108628A CA 1108628 A CA1108628 A CA 1108628A CA 329322 A CA329322 A CA 329322A CA 1108628 A CA1108628 A CA 1108628A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- aryl
- pyrrolin
- substituted
- 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
- CDCHBOQVXIGZHA-UHFFFAOYSA-N 1,2-dihydropyrrol-5-one Chemical class O=C1NCC=C1 CDCHBOQVXIGZHA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical group C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 230000000875 corresponding effect Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 10
- -1 napthyl Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 150000003235 pyrrolidines Chemical class 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 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 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229940073584 methylene chloride Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VNGGQUXNILKHIE-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC(=O)NC1 VNGGQUXNILKHIE-UHFFFAOYSA-N 0.000 description 2
- XWWQNFOFKPPMHY-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,5-dimethylpyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=C(Cl)C=C1 XWWQNFOFKPPMHY-UHFFFAOYSA-N 0.000 description 2
- CHVOVFFXIYWDTJ-UHFFFAOYSA-N 4-amino-3-[4-(trifluoromethyl)phenyl]butanoic acid hydrochloride Chemical compound Cl.OC(=O)CC(CN)C1=CC=C(C(F)(F)F)C=C1 CHVOVFFXIYWDTJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000005588 carbonic acid salt group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000007686 potassium Nutrition 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-XFXZXTDPSA-N (9Z)-12-hydroxyoctadec-9-enoic acid Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-XFXZXTDPSA-N 0.000 description 1
- RHNBWZZWDAOBQY-UHFFFAOYSA-N 1,2,4-trimethyl-3-phenyl-2h-pyrrol-5-one Chemical compound CC1N(C)C(=O)C(C)=C1C1=CC=CC=C1 RHNBWZZWDAOBQY-UHFFFAOYSA-N 0.000 description 1
- JWUYOFJPYSNYFC-UHFFFAOYSA-N 1,2-dimethyl-3,4-diphenyl-2h-pyrrol-5-one Chemical compound CC1N(C)C(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JWUYOFJPYSNYFC-UHFFFAOYSA-N 0.000 description 1
- QLCPYHKRCGVOOA-UHFFFAOYSA-N 1,2-dimethyl-3-phenyl-2h-pyrrol-5-one Chemical compound CC1N(C)C(=O)C=C1C1=CC=CC=C1 QLCPYHKRCGVOOA-UHFFFAOYSA-N 0.000 description 1
- WPPVBSYWZWZVTN-UHFFFAOYSA-N 1,3,5-trimethyl-4-phenylpyrrolidin-2-one Chemical compound CC1C(=O)N(C)C(C)C1C1=CC=CC=C1 WPPVBSYWZWZVTN-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HOEWCGCSKILLPY-UHFFFAOYSA-N 1,5-dimethyl-4-(4-nitrophenyl)pyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=C([N+]([O-])=O)C=C1 HOEWCGCSKILLPY-UHFFFAOYSA-N 0.000 description 1
- QPBIBMGRFHVCJI-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)-3-phenylpyrrolidin-2-one Chemical compound O=C1N(C)CC(C=2C=CC(C)=CC=2)C1C1=CC=CC=C1 QPBIBMGRFHVCJI-UHFFFAOYSA-N 0.000 description 1
- SWLVHCWYTKNOAB-UHFFFAOYSA-N 2-(5-oxo-3-phenyl-1,2-dihydropyrrol-4-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=C(C=2C=CC=CC=2)CNC1=O SWLVHCWYTKNOAB-UHFFFAOYSA-N 0.000 description 1
- APBKZMJARWKEJO-UHFFFAOYSA-N 2-amino-1-[4-(trifluoromethyl)phenyl]ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=C(C(F)(F)F)C=C1 APBKZMJARWKEJO-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical class NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 description 1
- GNWOFDWOUZXQPD-UHFFFAOYSA-N 3,4-diphenyl-1,2-dihydropyrrol-5-one Chemical compound O=C1NCC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GNWOFDWOUZXQPD-UHFFFAOYSA-N 0.000 description 1
- RVCBHJGJEHRCCK-UHFFFAOYSA-N 3-(2-fluorophenyl)-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound FC1=CC=CC=C1C1C(=O)NCC1C1=CC=C(C(F)(F)F)C=C1 RVCBHJGJEHRCCK-UHFFFAOYSA-N 0.000 description 1
- PMGYCIGYLNWVCH-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 PMGYCIGYLNWVCH-UHFFFAOYSA-N 0.000 description 1
- XZWCDKTUYKCMMH-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(=O)NCC1C1=CC=C(C(F)(F)F)C=C1 XZWCDKTUYKCMMH-UHFFFAOYSA-N 0.000 description 1
- XIAMSSUQNNNXMH-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 XIAMSSUQNNNXMH-UHFFFAOYSA-N 0.000 description 1
- SYUHPEZHTMIRMJ-UHFFFAOYSA-N 3-(4-fluorophenyl)-4-phenylpyrrolidin-2-one Chemical compound C1=CC(F)=CC=C1C1C(=O)NCC1C1=CC=CC=C1 SYUHPEZHTMIRMJ-UHFFFAOYSA-N 0.000 description 1
- LXZAVFHIIYGLTF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 LXZAVFHIIYGLTF-UHFFFAOYSA-N 0.000 description 1
- XRCJTMJEQCHAOB-UHFFFAOYSA-N 3-(4-methylphenyl)-4-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 XRCJTMJEQCHAOB-UHFFFAOYSA-N 0.000 description 1
- CVOQOLZRCXIRRT-UHFFFAOYSA-N 3-methyl-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1NC(=O)C(C)C1C1=CC=C(C(F)(F)F)C=C1 CVOQOLZRCXIRRT-UHFFFAOYSA-N 0.000 description 1
- USRGHTBNRODIGQ-UHFFFAOYSA-N 3-phenyl-4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 USRGHTBNRODIGQ-UHFFFAOYSA-N 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- JPMRXLUPEVYCNZ-UHFFFAOYSA-N 4-(2-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound FC1=CC=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CNC1=O JPMRXLUPEVYCNZ-UHFFFAOYSA-N 0.000 description 1
- PUUOYNFEZBLMMU-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-3-phenylpyrrolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 PUUOYNFEZBLMMU-UHFFFAOYSA-N 0.000 description 1
- JBIVTGWLCSEZEU-UHFFFAOYSA-N 4-(4-aminophenyl)-1,5-dimethylpyrrolidin-2-one Chemical compound C1C(=O)N(C)C(C)C1C1=CC=C(N)C=C1 JBIVTGWLCSEZEU-UHFFFAOYSA-N 0.000 description 1
- QZSANDZKAKLRPX-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(=CC=2)C(F)(F)F)CNC1=O QZSANDZKAKLRPX-UHFFFAOYSA-N 0.000 description 1
- LIOVPXGQAPGNNY-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-phenyl-1,2-dihydropyrrol-5-one Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC=CC=2)CNC1=O LIOVPXGQAPGNNY-UHFFFAOYSA-N 0.000 description 1
- SDVNHWAFTHMIQR-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-phenylpyrrolidin-2-one Chemical class C1=CC(F)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 SDVNHWAFTHMIQR-UHFFFAOYSA-N 0.000 description 1
- SSNGRNRNPOYPGF-UHFFFAOYSA-N 4-(4-methylphenyl)-3-phenylpyrrolidin-2-one Chemical compound C1=CC(C)=CC=C1C1C(C=2C=CC=CC=2)C(=O)NC1 SSNGRNRNPOYPGF-UHFFFAOYSA-N 0.000 description 1
- MUJPZGGZLAHFFQ-UHFFFAOYSA-N 4-(methylamino)-3-phenylpentanoic acid hydrochloride Chemical compound Cl.CNC(C)C(CC(O)=O)C1=CC=CC=C1 MUJPZGGZLAHFFQ-UHFFFAOYSA-N 0.000 description 1
- PDTLMKLERGEENQ-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CC(=O)NC1 PDTLMKLERGEENQ-UHFFFAOYSA-N 0.000 description 1
- CMLJIUSFVCLSEZ-UHFFFAOYSA-N 4-amino-2,3-diphenylbutanoic acid hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1 CMLJIUSFVCLSEZ-UHFFFAOYSA-N 0.000 description 1
- VKEIQQUWTUWPKS-UHFFFAOYSA-N 4-amino-2-(2-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]butanoic acid hydrochloride Chemical compound Cl.C=1C=C(C(F)(F)F)C=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1F VKEIQQUWTUWPKS-UHFFFAOYSA-N 0.000 description 1
- IEKAYFRWOBOQIQ-UHFFFAOYSA-N 4-amino-2-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]butanoic acid hydrochloride Chemical compound Cl.C=1C=C(C(F)(F)F)C=CC=1C(CN)C(C(O)=O)C1=CC=C(F)C=C1 IEKAYFRWOBOQIQ-UHFFFAOYSA-N 0.000 description 1
- AXKPDYZORRWBOD-UHFFFAOYSA-N 4-amino-2-(4-fluorophenyl)-3-phenylbutanoic acid hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CN)C(C(O)=O)C1=CC=C(F)C=C1 AXKPDYZORRWBOD-UHFFFAOYSA-N 0.000 description 1
- QFNWDPAAVSNPDY-UHFFFAOYSA-N 4-amino-3-(3,4-dimethoxyphenyl)-2-phenylbutanoic acid hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1C(CN)C(C(O)=O)C1=CC=CC=C1 QFNWDPAAVSNPDY-UHFFFAOYSA-N 0.000 description 1
- GAVYIBFSKZVARR-UHFFFAOYSA-N 4-amino-3-(4-fluorophenyl)-2-phenylbutanoic acid hydrochloride Chemical compound Cl.C=1C=C(F)C=CC=1C(CN)C(C(O)=O)C1=CC=CC=C1 GAVYIBFSKZVARR-UHFFFAOYSA-N 0.000 description 1
- YSAFGIWSLMRCEH-UHFFFAOYSA-N 4-amino-3-(4-methylphenyl)-2-phenylbutanoic acid hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(CN)C(C(O)=O)C1=CC=CC=C1 YSAFGIWSLMRCEH-UHFFFAOYSA-N 0.000 description 1
- DQOSOTIKDZAXKT-UHFFFAOYSA-N 4-phenyl-3-[4-(trifluoromethyl)phenyl]-1,2-dihydropyrrol-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)NC1 DQOSOTIKDZAXKT-UHFFFAOYSA-N 0.000 description 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- JHRDATNCTTVZBE-UHFFFAOYSA-N Cl.OC(=O)C(C)C(CN)C1=CC=C(C(F)(F)F)C=C1 Chemical compound Cl.OC(=O)C(C)C(CN)C1=CC=C(C(F)(F)F)C=C1 JHRDATNCTTVZBE-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910010277 boron hydride Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DJEBTLRMBZNIIF-UHFFFAOYSA-N n-phenacyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)CC1=CC=CC=C1 DJEBTLRMBZNIIF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91468278A | 1978-06-12 | 1978-06-12 | |
| US914,682 | 1978-06-12 | ||
| US1249679A | 1979-02-15 | 1979-02-15 | |
| US12,496 | 1979-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108628A true CA1108628A (en) | 1981-09-08 |
Family
ID=26683628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA329,322A Expired CA1108628A (en) | 1978-06-12 | 1979-06-08 | Production of pyrrolidin-2-ones from 2-pyrrolin-2- ones and the production of 3-pyrrolin-2-ones |
Country Status (19)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943640A (en) * | 1983-10-14 | 1990-07-24 | The Dow Chemical Company | Preparation of 5-(1-alkyl-carbonyloxy)alkylpyrrolidin-2-one |
| WO1990007499A1 (en) * | 1988-12-27 | 1990-07-12 | Ici Americas Inc. | Process for the preparation of 3-carboalkoxypyrrolidones |
| US5021587A (en) * | 1990-01-24 | 1991-06-04 | Petrolite Corporation | Synthesis of N,3,4-trisubstituted-3-azoline-2-ones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272842A (en) * | 1965-06-25 | 1966-09-13 | Lilly Co Eli | Novel pyrrolinones |
| GB1350582A (en) * | 1970-07-24 | 1974-04-18 | Ucb Sa | Cerivatives of 2-pyrrolidinone |
| DE2413935A1 (de) | 1974-03-20 | 1975-10-16 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone |
-
1979
- 1979-05-14 IL IL57266A patent/IL57266A/xx unknown
- 1979-05-15 GR GR59088A patent/GR68438B/el unknown
- 1979-05-17 AR AR276559A patent/AR222997A1/es active
- 1979-05-28 AT AT793866A patent/ATA386679A/de not_active Application Discontinuation
- 1979-06-01 AU AU47670/79A patent/AU529479B2/en not_active Ceased
- 1979-06-01 PT PT69716A patent/PT69716A/pt unknown
- 1979-06-06 ES ES481315A patent/ES481315A1/es not_active Expired
- 1979-06-08 CA CA329,322A patent/CA1108628A/en not_active Expired
- 1979-06-09 DE DE2954236A patent/DE2954236C2/de not_active Expired
- 1979-06-09 DE DE2954237A patent/DE2954237C2/de not_active Expired
- 1979-06-09 DE DE19792923553 patent/DE2923553A1/de active Granted
- 1979-06-11 NO NO791943A patent/NO791943L/no unknown
- 1979-06-11 IT IT49373/79A patent/IT1116891B/it active
- 1979-06-11 FR FR7914907A patent/FR2434151A1/fr active Granted
- 1979-06-11 SE SE7905079A patent/SE431644B/sv not_active IP Right Cessation
- 1979-06-11 GB GB7920275A patent/GB2028307B/en not_active Expired
- 1979-06-11 DK DK241779A patent/DK157847C/da not_active IP Right Cessation
- 1979-06-12 NL NL7904584A patent/NL7904584A/xx not_active Application Discontinuation
- 1979-06-12 FI FI791866A patent/FI70209C/fi not_active IP Right Cessation
- 1979-06-12 CH CH5496/79A patent/CH650772A5/de not_active IP Right Cessation
- 1979-06-12 NZ NZ190705A patent/NZ190705A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI70209B (fi) | 1986-02-28 |
| DE2923553A1 (de) | 1979-12-20 |
| DK157847C (da) | 1990-09-17 |
| CH650772A5 (de) | 1985-08-15 |
| AU529479B2 (en) | 1983-06-09 |
| DE2954236C2 (enrdf_load_stackoverflow) | 1988-10-06 |
| IL57266A0 (en) | 1979-09-30 |
| GB2028307B (en) | 1983-01-19 |
| SE7905079L (sv) | 1979-12-13 |
| FI70209C (fi) | 1986-09-15 |
| AU4767079A (en) | 1979-12-20 |
| NO791943L (no) | 1979-12-13 |
| IT1116891B (it) | 1986-02-10 |
| FI791866A7 (fi) | 1979-12-13 |
| DK157847B (da) | 1990-02-26 |
| FR2434151B3 (enrdf_load_stackoverflow) | 1982-04-30 |
| NL7904584A (nl) | 1979-12-14 |
| NZ190705A (en) | 1981-10-19 |
| IL57266A (en) | 1982-12-31 |
| FR2434151A1 (fr) | 1980-03-21 |
| GB2028307A (en) | 1980-03-05 |
| DE2954237C2 (enrdf_load_stackoverflow) | 1989-09-21 |
| PT69716A (en) | 1979-07-01 |
| DK241779A (da) | 1979-12-13 |
| AR222997A1 (es) | 1981-07-15 |
| DE2923553C2 (enrdf_load_stackoverflow) | 1988-06-01 |
| IT7949373A0 (it) | 1979-06-11 |
| ES481315A1 (es) | 1980-08-16 |
| GR68438B (enrdf_load_stackoverflow) | 1981-12-30 |
| ATA386679A (de) | 1983-12-15 |
| SE431644B (sv) | 1984-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |