2-oxo-4-phenylpyrrolidine-3-carboxylic acid
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
In toluene for 5h; Reflux; | 100% |
at 190℃; for 0.5h; | 58% |
at 175℃; |
4-nitro-3-phenylbutanoic acid methyl ester
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 45004.5 Torr; | 92% |
With hydrogen; platinum(IV) oxide In methanol for 20h; | 72% |
With hydrogen; nickel In methanol at 60℃; |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol at 0 - 20℃; for 1h; | 92% |
ethyl 3-phenyl-4-nitrobutanoate
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In ethanol at 0℃; for 2h; | 88% |
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In ethanol at 0℃; for 2h; | 82% |
With hydrogen; palladium on activated charcoal 1.) 2.) toluene, reflux; Yield given. Multistep reaction; | |
Stage #1: ethyl 3-phenyl-4-nitrobutanoate With hydrogen In ethanol at 20℃; under 1034.32 Torr; Stage #2: In ethanol; toluene Reflux; |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: C11H11N3O3 In chloroform at 60℃; for 3h; Inert atmosphere; Stage #2: With dmap In chloroform at 20℃; for 2h; Inert atmosphere; | 87% |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel(II) chloride hexahydrate; water In dichloromethane at -10 - 30℃; for 5h; Concentration; Reagent/catalyst; Temperature; | 85% |
4-amino-3-phenylbutanoic acid methyl ester
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With triethylamine In ethanol Reflux; | 83% |
(+/-)-4-nitro-3-phenylbutyric acid 4'-(4-nitro-3-phenylbutyryloxymethyl)-[2,2']bipyridinyl-4-ylmethyl ester
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With polymer-supported borohydride resin; nickel dichloride In dichloromethane at 20℃; | 60% |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 95℃; for 6h; Sealed tube; | 59% |
3-cyano-3-phenylpropanoic acid ethyl ester
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 3-cyano-3-phenylpropanoic acid ethyl ester With sodium tetrahydroborate; cobalt(II) chloride hexahydrate In tetrahydrofuran; water at 0 - 20℃; for 72h; Stage #2: With ammonia In tetrahydrofuran; water | 57% |
Multi-step reaction with 2 steps 1: H2, conc. HCl / 10percent Pd/C / methanol / 2068.6 Torr 2: Et3N / toluene / Heating View Scheme |
Conditions | Yield |
---|---|
With aluminum (III) chloride; sodium chloride at 0 - 180℃; under 750.075 Torr; | 44% |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride; zinc In ethanol Heating; | 36% |
(2-nitro-1-phenyl-ethyl)-malonic acid dimethyl ester
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With palladium on activated carbon; hydrogen In o-xylene at 130℃; under 11251.1 Torr; for 18h; Catalytic behavior; | 35% |
Multi-step reaction with 3 steps 1: hydrogen / methanol / 2.5 h / 20 °C / 3102.97 Torr 2: sodium hydroxide / ethanol / 48 h / 20 °C 3: toluene / 5 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With aluminum (III) chloride; sodium chloride at 0 - 180℃; under 750.075 Torr; | 32% |
2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; water | |
Multi-step reaction with 2 steps 1: ethanolic KOH 2: 175 °C View Scheme | |
With sodium carbonate for 6h; Reagent/catalyst; Reflux; | 3.3 g |
Conditions | Yield |
---|---|
With potassium hydroxide |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With triethylamine In toluene Heating; |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With diethyl ether; nickel at 70 - 90℃; Hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / 1,1,3,3-tetramethylguanidine / 3 h / Heating 2: 72 percent / H2 / PtO2 / methanol / 20 h View Scheme | |
Multi-step reaction with 2 steps 1: 1,1,3,3-tetramethylguanidine / 70 °C 2: H2 / Raney nickel / methanol / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol 2: hydrogen / platinum(IV) oxide / ethanol View Scheme | |
Multi-step reaction with 3 steps 1: N,N,N',N'-tetramethylguanidine / 42 h / 20 °C 2: palladium 10% on activated carbon; acetic acid; hydrogen / dichloromethane / 20 °C 3: triethylamine / ethanol / Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol; H2O / 60 °C 2: H2, conc. HCl / 10percent Pd/C / methanol / 2068.6 Torr 3: Et3N / toluene / Heating View Scheme |
3-methoxycarbonyl-4-phenyl-2-pyrrolidone
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89.6 percent / 10percent aq. KOH / 5 h / Heating 2: 58 percent / 0.5 h / 190 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 48 h / 20 °C 2: toluene / 5 h / Reflux View Scheme |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetic acid / chloroform / 1 h / 0 - 20 °C 1.2: 20 °C 2.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 3.1: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C View Scheme |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 2: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: cesium fluoride; tetrabutyl-ammonium chloride; bis-triphenylphosphine-palladium(II) chloride / toluene; water / 18 h / 20 °C / Inert atmosphere 2.1: acetic acid / chloroform / 1 h / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 4.1: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 2.1: hydrogen / ethanol / 20 °C / 1034.32 Torr 2.2: Reflux View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 24 h / 20 - 30 °C 2: nickel(II) chloride hexahydrate; water; sodium tetrahydroborate / dichloromethane / 5 h / -10 - 30 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C 3.1: hydrogen / ethanol / 20 °C / 1034.32 Torr 3.2: Reflux View Scheme | |
Multi-step reaction with 2 steps 1: aminopropyl-silica-based catalyst; dimethylaminopropyl-silica-based solid / o-xylene / 18 h / 70 °C / Green chemistry 2: palladium on activated carbon; hydrogen / o-xylene / 18 h / 130 °C / 11251.1 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere 1.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr 3.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: calcined hydrotalcite / ethanol / 24 h / Reflux 2: nickel(II) chloride hexahydrate; sodium tetrahydroborate / ethanol / 2 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 24 h / 25 °C 2: calcined hydrotalcite / 24 h / Reflux 3: nickel(II) chloride hexahydrate; sodium tetrahydroborate / ethanol / 2 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite; potassium bromide / water; dichloromethane / 0.21 h / 0 °C 2.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere 2.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr 4.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr View Scheme |
4-phenylpyrrolidin-2-one
propargyl bromide
N-propargyl-4-phenyl-2-pyrrolidone
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran at 0 - 20℃; for 6h; | 97% |
4-phenylpyrrolidin-2-one
(R)-1-(1-naphthyl)ethyl isocyanate
N-<(R)-1-(1-naphthyl)ethyl>-4-phenyl-2-pyrrolidone-1-carboxamide
Conditions | Yield |
---|---|
In benzene for 24h; Heating; | 95% |
4-phenylpyrrolidin-2-one
1,1,1,3,3,3-hexamethyl-disilazane
4-phenyl-1-(trimethylsilyl)-2-pyrrolidinone
Conditions | Yield |
---|---|
With hydrogenchloride for 0.333333h; Heating; | 90% |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With hydrogenchloride; water for 12h; Reflux; | 88% |
With hydrogenchloride In water for 12h; Reflux; | 88% |
With hydrogenchloride In water for 16h; Sealed tube; Reflux; | 65% |
With hydrogenchloride; water In water for 16h; Reflux; | 55% |
4-phenylpyrrolidin-2-one
methyl iodide
1-methyl-4-phenyl-pyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 4-phenylpyrrolidin-2-one With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Sealed tube; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; Sealed tube; Inert atmosphere; | 88% |
4-phenylpyrrolidin-2-one
methyl chloroacetate
methyl-2-oxo-4-phenylpyrrolidine-1-acetate
Conditions | Yield |
---|---|
Stage #1: 4-phenylpyrrolidin-2-one With potassium tert-butylate In N,N-dimethyl-formamide at -10℃; for 2h; Stage #2: methyl chloroacetate In N,N-dimethyl-formamide at -10 - 0℃; for 2h; Concentration; Temperature; Solvent; | 84% |
With sodium methylate 1.) toluene, 150-160 deg C, 2.) toluene, 60-70 deg C, 2 h; Yield given. Multistep reaction; | |
In tetrahydrofuran; water; mineral oil |
4-phenylpyrrolidin-2-one
3-bromo-5-[methyl(methylsulfonyl)amino]benzoic acid methyl ester
3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidine-1-yl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 7h; | 82% |
4-phenylpyrrolidin-2-one
triethyloxonium fluoroborate
Ethoxy-2 phenyl-4 Δ1-pyrroline
Conditions | Yield |
---|---|
81% |
Conditions | Yield |
---|---|
With triethylamine In toluene | 76.5% |
formaldehyd
4-phenylpyrrolidin-2-one
1-chloromethyl-4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With chloro-trimethyl-silane for 1h; Heating; | 67.5% |
Conditions | Yield |
---|---|
With thionyl chloride; triethylamine In toluene | A 58.5% B 65.4% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; 1,3-bis(methylamino)propane In 1,4-dioxane for 24h; Reflux; | 60% |
4-phenylpyrrolidin-2-one
4-iodo-N-(quinolin-8-yl)benzamide
C26H21N3O2
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 140℃; Microwave irradiation; | 59% |
Conditions | Yield |
---|---|
In tetrahydrofuran | 57% |
4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h; Inert atmosphere; | 55% |
4-phenylpyrrolidin-2-one
benzyl bromide
1-benzyl-4-phenylpyrrolidin-2-one
Conditions | Yield |
---|---|
With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; | 52% |
With sodium hydride 1.) xylene, reflux, 5 h, 2.) xylene, reflux, 4 h; Yield given. Multistep reaction; |
4-phenylpyrrolidin-2-one
1-(2,2,2-trifluoroacetyl)indolin-5-ylsulfonyl chloride
Conditions | Yield |
---|---|
Stage #1: 4-phenylpyrrolidin-2-one With n-butyllithium In tetrahydrofuran for 0.5h; Stage #2: 1-(2,2,2-trifluoroacetyl)indolin-5-ylsulfonyl chloride In tetrahydrofuran at 0℃; for 4h; | 45% |
4-phenylpyrrolidin-2-one
4-phenyl-2-pyrrolidinethione
Conditions | Yield |
---|---|
With diphosphorus pentasulfide In o-xylene Heating; | 40% |
Conditions | Yield |
---|---|
Stage #1: 4-phenylpyrrolidin-2-one With sodium hydride In N,N-dimethyl-formamide at 20 - 50℃; for 1h; Metallation; Stage #2: 2-(diethylamino)ethyl chloride In N,N-dimethyl-formamide at 80℃; for 8h; Alkylation; Stage #3: oxalic acid In diethyl ether; ethanol acid-base reaction; | 37.5% |
Empirical Formula of 4-Phenylpyrrolidone-2 (CAS NO.1198-97-6): C10H11NO
Molecular Weight: 161.2004 g/mol
Index of Refraction: 1.55
Density: 1.108 g/cm3
Flash Point: 212.4 °C
Enthalpy of Vaporization: 60.82 kJ/mol
Boiling Point: 362.3 °C at 760 mmHg
Vapour Pressure: 1.96E-05 mmHg at 25 °C
Structure of 4-Phenylpyrrolidone-2 (CAS NO.1198-97-6):
IUPAC Name of 4-Phenylpyrrolidone-2 (CAS NO.1198-97-6): 4-Phenylpyrrolidin-2-one
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | unreported | 352mg/kg (352mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ANALGESIA | Russian Pharmacology and Toxicology Vol. 44, Pg. 22, 1981. |
mouse | LD50 | intraperitoneal | 325mg/kg (325mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Archivum Immunologiae et Therapiae Experimentalis. Vol. 23, Pg. 733, 1975. |
mouse | LD50 | unreported | 352mg/kg (352mg/kg) | AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS | Pharmaceutical Chemistry Journal Vol. 14, Pg. 776, 1980. |
Poison by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
4-Phenylpyrrolidone-2 ,its cas register number is 1198-97-6. It also can be called 4-Phenyl-2-pyrrolidinone ; 2-Pyrrolidinone, 4-phenyl- ;and Phenylpyrrolidone .
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