3-iodopyridine
ethanol
carbon monoxide
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate at 20 - 125℃; under 7500.75 - 22502.3 Torr; for 0.333333h; microwave irradiation; | 98% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 80℃; under 760.051 Torr; for 6h; | 94% |
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; under 9308.91 Torr; | |
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; under 8274.59 - 10136.4 Torr; | 88 %Spectr. |
With palladium diacetate; potassium carbonate at 60℃; under 20521.4 Torr; for 12h; Green chemistry; chemoselective reaction; | 21 %Spectr. |
3-Bromopyridine
ethanol
carbon monoxide
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine at 70℃; under 760.051 Torr; for 3h; Catalytic behavior; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid In toluene at 55℃; for 4h; | 97.2% |
With sulfuric acid for 10h; Reflux; Sealed tube; | 83% |
With sulfuric acid for 4h; Reflux; | 81% |
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile for 2h; Heating; | 92% |
1-(pyridin-3-yl)pentan-1-one
ethyl trifluoroacetate,
A
3-pyridinecarboxylic acid ethyl ester
B
1,1,1-trifluoro-2-hexanone
Conditions | Yield |
---|---|
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 1-(pyridin-3-yl)pentan-1-one In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Schlenk technique; Reflux; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; | A 92% B n/a |
dicobalt octacarbonyl
ethanol
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate at 50℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 91% |
dicobalt octacarbonyl
ethanol
pyridin-3-yl trifluoromethanesulfonate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate at 50℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 90% |
3-iodopyridine
ethanol
molybdenum hexacarbonyl
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N-ethyl-N,N-diisopropylamine In neat (no solvent) at 130℃; for 0.333333h; Microwave irradiation; | 89% |
1-oxy-nicotinic acid ethyl ester
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate; zinc In methanol at 20℃; for 2.5h; | 87% |
Conditions | Yield |
---|---|
microwave irradiation; | 86% |
In toluene at 110℃; for 24h; | 81% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 40℃; for 5h; | 86% |
With chloro-trimethyl-silane at 20 - 40℃; for 5h; Inert atmosphere; | 86% |
3-Chloropyridine
dicobalt octacarbonyl
ethanol
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With (S)-1-[(R)-2-(di-1-naphthylphosphino)ferrocenyl]ethyl-di-tert.-butylphosphine; potassium acetate; palladium diacetate at 80℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 86% |
ethyl bromide
potassium nicotinate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With tetrabutylammomium bromide for 43h; Ambient temperature; | 82% |
3-Bromopyridine
potassium monoethyl oxalate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane In 1-methyl-pyrrolidin-2-one at 150℃; for 16h; Inert atmosphere; | 82% |
nicotinic acid
boron trifluoride diethyl etherate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 120℃; | 82% |
tetraethoxy tellurium(IV)
nicotinamide
A
pyridine-3-carbonitrile
B
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
In tetrachloromethane for 18h; Heating; | A 8% B 79% |
nicotinamide
A
pyridine-3-carbonitrile
B
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With tetraethoxy tellurium(IV) In tetrachloromethane for 18h; Heating; | A 8% B 79% |
3-iodopyridine
potassium monoethyl oxalate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With palladium diacetate In 1-methyl-pyrrolidin-2-one at 20 - 140℃; for 24h; Inert atmosphere; | 79% |
3-Bromopyridine
dicobalt octacarbonyl
ethanol
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With dmap; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 0.5h; Microwave irradiation; | 78% |
Conditions | Yield |
---|---|
With 1,3-diazido-propane In neat (no solvent) at 20℃; for 0.333333h; | 78% |
ethyl 6-iodonicotinate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; phenylsilane; indium(III) acetate In ethanol at 20℃; for 18h; | 75% |
With indium In water for 10h; Heating; | 64% |
With indium; water for 10h; Reflux; | 64% |
ethyl trifluoroacetate,
C12H11NOS
A
3-pyridinecarboxylic acid ethyl ester
B
1,1,1-trifluoro-4-(2-thiophenyl)butan-2-one
Conditions | Yield |
---|---|
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: C12H11NOS In tetrahydrofuran at 0℃; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; | A 75% B 74% |
piperidine
3-Chloropyridine
carbon monoxide
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; sodium phenoxide; palladium diacetate In toluene at 100℃; under 760.051 Torr; for 16h; | 71% |
3-Chloropyridine
ethanol
carbon monoxide
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride; sodium acetate; 1,4-di(diphenylphosphino)-butane at 100℃; under 750.075 Torr; for 16h; | 71% |
Conditions | Yield |
---|---|
With Josiphos Et2P-Fc-PtBu2 ligand; sodium acetate; palladium diacetate at 130 - 135℃; under 2068.59 Torr; for 20h; | 70% |
pyrrole
ethyl 2-bromo-2-diazoacetate
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium dithionite; c-type cytochrome maquette, C45 In ethanol at 5℃; for 2h; pH=8.6; Sealed tube; Inert atmosphere; Enzymatic reaction; | 69.4% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate for 144h; Heating; | 67% |
With iron(III) chloride for 21h; Heating; | 63.3% |
3-Bromopyridine
oxalic acid diethyl ester
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With dmap; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.333333h; Microwave irradiation; | 66% |
Propargylamine
propynoic acid ethyl ester
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; silver trifluoromethanesulfonate In toluene at 80℃; for 6h; Sealed tube; regioselective reaction; | 63% |
3-pyridinecarboxaldehyde
ethanol
A
3-pyridinecarboxylic acid ethyl ester
B
1,2-di(pyridine-3-yl)ethane-1,2-dione
Conditions | Yield |
---|---|
With oxygen; Thiamine hydrochloride; triethylamine for 2h; Reflux; | A 30% B 58% |
2-aminobutanol
3-pyridinecarboxylic acid ethyl ester
N-(1-hydroxybutan-2-yl)nicotinamide
Conditions | Yield |
---|---|
at 50℃; for 0.5h; | 100% |
3-pyridinecarboxylic acid ethyl ester
3-amino-2-propanol
N-(2-hydroxypropyl)-3-pyridinecarboxamide
Conditions | Yield |
---|---|
at 50℃; for 0.5h; | 100% |
3-pyridinecarboxylic acid ethyl ester
propan-1-ol-3-amine
N-(3-hydroxypropyl)nicotinamide
Conditions | Yield |
---|---|
at 50℃; for 0.5h; | 100% |
3-pyridinecarboxylic acid ethyl ester
1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene
Conditions | Yield |
---|---|
In acetonitrile for 6h; Heating; | 100% |
Conditions | Yield |
---|---|
at 80 - 85℃; for 6.5h; | 99.5% |
3-pyridinecarboxylic acid ethyl ester
Ethyl nipecotate
Conditions | Yield |
---|---|
With hydrogen In hexane at 100℃; under 7600.51 Torr; for 24h; Temperature; Pressure; Autoclave; | 99% |
With sodium hydroxide; hydrogen; nickel In ethanol; water at 20 - 40℃; Electrolysis; | 98% |
With 1,4-dioxane; nickel at 165℃; under 110326 - 220652 Torr; Hydrogenation; |
3-pyridinecarboxylic acid ethyl ester
benzyl bromide
N-benzyl-3-(ethoxycarbonyl)pyridinium bromide
Conditions | Yield |
---|---|
In isopropyl alcohol for 18h; | 98% |
In isopropyl alcohol at 20℃; for 18h; | 90% |
In nitrobenzene at 40℃; Rate constant; | |
In acetone Reflux; |
Conditions | Yield |
---|---|
With PPA at 155℃; for 4.5h; | 98% |
With alkaline H2O In dimethyl sulfoxide at 30℃; Rate constant; other solvent (EtOH); variation of water concentrations; | |
esterase in WBN; IL-Ht rat abdominal skin homogenate at 37℃; Enzyme kinetics; |
3-pyridinecarboxylic acid ethyl ester
N-(N,N-diethylaminomethyl)-2-piperidone
Conditions | Yield |
---|---|
With sodium hydride In toluene for 8h; Heating; | 97% |
Conditions | Yield |
---|---|
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃; | 97% |
Multi-step reaction with 2 steps 1: diethyl ether; lithium alanate 2: lead (IV)-acetate; benzene View Scheme |
3-pyridinecarboxylic acid ethyl ester
ethanolamine
N-(2-hydroxyethyl)nicotinamide
Conditions | Yield |
---|---|
Stage #1: 3-pyridinecarboxylic acid ethyl ester; ethanolamine at 125℃; for 4h; Large scale; Stage #2: With acetone at 45 - 60℃; for 1h; Large scale; Stage #3: at 10 - 30℃; for 2.5h; Temperature; Large scale; | 96.6% |
64.5% | |
64.5% |
3-pyridinecarboxylic acid ethyl ester
guanidine hydrochloride
N-(pyridyl-3-carbonyl)guanidine
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 12h; Heating; | 95% |
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 36h; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran dry Ar-flushed Schlenk flask charged with organic compound, soln. of base added dropwise, stirred at -78 °C for 15 min; | 95% |
Conditions | Yield |
---|---|
Stage #1: 3-pyridinecarboxylic acid ethyl ester; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C10H10BrN3O With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction; | 95% |
Conditions | Yield |
---|---|
Stage #1: 3-pyridinecarboxylic acid ethyl ester With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; P,P'-(1,2-ethanediyl)bis{bis[3,5-di(trifluoromethyl)phenyl]phosphane} In toluene for 0.0833333h; Inert atmosphere; Microwave irradiation; Stage #2: methyl methacrylate In toluene at 120℃; for 24h; Inert atmosphere; Microwave irradiation; Sealed tube; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
With hydrazine hydrate monohydrate In methanol at 140℃; for 1h; Microwave irradiation; Sealed tube; | 93% |
With hydrazine hydrate In ethanol for 1.08333h; Ambient temperature; | 85% |
With hydrazine hydrate In ethanol Reflux; Sealed tube; | 85% |
3-pyridinecarboxylic acid ethyl ester
2,2,2-trifluoroethyl(phenyl)iodonium trifluoromethanesulfonate
N-(2,2,2-Trifluoroethyl)-3-(ethoxycarbonyl)pyridinium triflate
Conditions | Yield |
---|---|
In dichloromethane for 0.166667h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With graphene oxide In neat (no solvent) at 100℃; for 18h; Sealed tube; | 92% |
With silica gel In neat (no solvent) at 100℃; for 12h; Inert atmosphere; Sealed tube; | 87% |
3-pyridinecarboxylic acid ethyl ester
mesitylenesulfonylhydroxylamine
2,4,6-Trimethyl-benzenesulfonate1-amino-3-ethoxycarbonyl-pyridinium;
Conditions | Yield |
---|---|
In dichloromethane for 0.5h; Ambient temperature; | 92% |
3-pyridinecarboxylic acid ethyl ester
3-(4-bromophenyl)-2-methylquinazolin-4(3H)-one
2-[2-Oxo-2-(3-pyridyl)ethyl]-3-p-bromophenyl-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane Heating; | 92% |
2.43 g (92%) |
3-pyridinecarboxylic acid ethyl ester
acetic anhydride
ethyl 1-acetyl-1,4,5,6-tetrahydropyridine-3-carboxylate
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal under 5171.48 Torr; | 92% |
3-pyridinecarboxylic acid ethyl ester
ethyl acetate
A
3-oxo-3-pyridin-3-yl-propionic acid ethyl ester
B
ethyl acetoacetate
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -40℃; for 0.333333h; Claisen condensation; Inert atmosphere; | A 92% B n/a |
3-pyridinecarboxylic acid ethyl ester
Conditions | Yield |
---|---|
In acetonitrile for 60h; Inert atmosphere; Reflux; | 92% |
3-pyridinecarboxylic acid ethyl ester
methyl iodide
3-(ethoxycarbonyl)-1-methylpyridin-1-ium iodide
Conditions | Yield |
---|---|
In nitromethane for 12h; Ambient temperature; | 91% |
In isopropyl alcohol for 18h; | 87% |
In nitrobenzene at 35℃; Rate constant; |
Molecular Structure of Ethyl nicotinoate (CAS NO.614-18-6):
IUPAC Name:ethyl pyridine-3-carboxylate
Molecular Formula: C8H9NO2
Molecular Weight: 151.162560 g/mol
Melting Point: 8-10 °C(lit.)
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 39.19 Å2
Index of Refraction: 1.506
Molar Refractivity: 40.75 cm3
Molar Volume: 137 cm3
Surface Tension: 40.6 dyne/cm
Density: 1.102 g/cm3
Flash Point: 93.3 °C
Enthalpy of Vaporization: 46.05 kJ/mol
Boiling Point: 224 °C at 760 mmHg
Vapour Pressure: 0.0934 mmHg at 25°C
Storage temp: 2-8°C
Water Solubility: miscible
Chemical Properties: clear colourless to yellow liquid
Synonyms of Ethyl nicotinoate(CAS NO.614-18-6): nicotinic acid ethyl ester ; ethyl 3-pyridinecarboxylate ; ethyl pyridine-3-carboxylate ; ethyl nicotinate ; ethyl nicotinoate ; 3-pyridinecarboxylic acid ethyl ester ; 3-(ethoxycarbonyl)pyridine
Safety Information of Ethyl nicotinoate(CAS NO.614-18-6):
Hazard Codes: Xi
Risk Statements: 37/38-41-36/38-36/37/38
37/38:Irritating to respiratory system and skin
41:Risk of serious damage to eyes
36/38:Irritating to eyes and skin
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-39-37/39-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
39:Wear eye/face protection
37/39:Wear suitable gloves and eye/face protection
36:Wear suitable protective clothing
Ethyl nicotinoate (CAS NO.614-18-6) should be stored in a cool and a tightly closed container, can be used in organic synthesis.
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