Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In methanol for 0.0166667h; Ambient temperature; | 98% |
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h; | 98% |
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction; | 96% |
With potassium carbonate In water at 20℃; for 2h; | 89% |
With dibromamine-T; potassium carbonate at 20℃; for 1h; | 83% |
pyridine-4-carboxylic acid
methanol
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 24h; Heating; | 95% |
With sulfuric acid for 72h; Reflux; | 92% |
With sulfuric acid Reflux; | 80% |
methanol
isonicotinic acid ethylester
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With lanthanum complex grafted upon hydrotalcite for 4h; pH=10; Reflux; | 95% |
methanol
potassium pyridine-4-carboxylate
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With tetrachloromethane; triphenylphosphine at 55 - 60℃; | 91% |
4-Chloropyridine
methanol
carbon monoxide
lithium methanolate
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; 5 mol% Pd/C; sodium fluoride In 1,4-dioxane at 150℃; Inert atmosphere; | 88% |
pyridine-4-carboxylic acid
methyl iodide
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; | 85% |
picoline
methanol
A
4-pyridinecarboxylic acid, methyl ester
B
4-trichloromethyl-pyridine
Conditions | Yield |
---|---|
Stage #1: picoline With thionyl chloride for 3h; Reflux; Stage #2: methanol In water | A 18% B 82% |
methanol
1-(4-pyridyl)-1-propanone
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating; | 71% |
Conditions | Yield |
---|---|
With methanol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform at 20℃; for 1h; | 70% |
pyridine-4-carboxylic acid
carbonic acid dimethyl ester
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With sulfuric acid for 17h; Neat (no solvent); Reflux; | 67.5% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate for 108h; Heating; | 63% |
With iron(III) chloride for 32h; Heating; | 59% |
pyridine-4-carboxylic acid
methyl iodide
A
4-pyridinecarboxylic acid, methyl ester
B
4-methoxycarbonyl-1-methylpyridinium cation
Conditions | Yield |
---|---|
Stage #1: pyridine-4-carboxylic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h; Stage #2: methyl iodide In acetone at 20℃; for 4h; | A 62% B n/a |
Conditions | Yield |
---|---|
With manganese(IV) oxide; sodium cyanide; acetic acid In tetrahydrofuran at 20℃; for 72h; | 55% |
Stage #1: methanol With sodium tetrachloroaurate(III) dihyrate; potassium carbonate at 20℃; for 0.0166667h; Green chemistry; Stage #2: pyridine-4-methanol at 20℃; for 0.0333333h; Green chemistry; Stage #3: With oxygen at 80℃; under 760.051 Torr; Autoclave; Green chemistry; | 2 %Chromat. |
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With CH3OH In dichloromethane MeOH added under N2 to soln. of Pd complex in CH2Cl2, kept for 24 h; evapd. under reduced pressure, extd. with Et2O, evapd., dissolved in CD2Cl2; identified by NMR; | 54% |
methyl 3-(methylsulfonyloxy)-1-tosyl-1,2,3,6-tetrahydropyridine-4-carboxylate
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at -78 - 0℃; | 53% |
N-benzyl-4-(carbomethoxy)pyridinyl
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
In acetonitrile Product distribution; Quantum yield; Irradiation; | 51% |
methyl (4-pyridyl) ketone
methanol
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating; | 42% |
methanol
isoniazid
A
pyridine-4-carboxylic acid
B
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 10℃; for 6h; | A n/a B 40% |
methyl isonicotinate N-oxide
N,N-Dimethylthiocarbamoyl chloride
B
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
In acetonitrile at 81℃; for 4h; | A 30% B 35% |
methanol
isonicotinoyl chloride hydrochloride
4-pyridinecarboxylic acid, methyl ester
diazomethane
pyridine-4-carboxylic acid
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
In diethyl ether |
1,2-Dimethyl-4-oxo-8-(pyridine-4-carbonyl)-1,8-diaza-spiro[4.5]deca-2,6,9-triene-3-carboxylic acid ethyl ester
A
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With methanol Ambient temperature; |
n-propyl isonicotinate
methyl iodide
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
1) Et4NBF4, electrolysis; Yield given. Multistep reaction; |
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
durch Destillation im Wasserstoffstrom; |
A
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
at 59.9℃; Thermodynamic data; gas-phase; |
Conditions | Yield |
---|---|
With sulfuric acid; sodium carbonate In methanol | |
Multi-step reaction with 2 steps 1.1: thionyl chloride / 0.17 h / 0 - 20 °C / Inert atmosphere 2.1: 0.17 h / 0 - 20 °C 2.2: pH ~ 6 View Scheme |
1H-benzimidazol-2-amine
A
4-pyridinecarboxylic acid, methyl ester
B
N-(1H-benzoimidazol-2-yl)-nicotinamide
Conditions | Yield |
---|---|
In methanol |
3-methyl-4-cyanopyridine
4-pyridinecarboxylic acid, methyl ester
3-(2-oxo-2-pyridin-4-yl-ethyl)isonicotinonitrile
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane at 95℃; for 16h; | 100% |
With sodium hydride In 1,2-dimethoxyethane at 95℃; | 100% |
Conditions | Yield |
---|---|
In chloroform for 0.0833333h; | 100% |
4-pyridinecarboxylic acid, methyl ester
mesitylenesulfonylhydroxylamine
1-amino-4-(methoxycarbonyl)pyridin-1-ium 2,4,6-trimethylbenzene-1-sulfonate
Conditions | Yield |
---|---|
Stage #1: 4-pyridinecarboxylic acid, methyl ester; mesitylenesulfonylhydroxylamine In acetonitrile at 30℃; for 0.0166667h; Flow reactor; Stage #2: With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 0.0433333h; Flow reactor; | 100% |
In dichloromethane at 0 - 20℃; for 21h; Inert atmosphere; | 72% |
4-pyridinecarboxylic acid, methyl ester
benzyl bromide
1-benzyl-4-(methoxycarbonyl)pyridin-1-ium
Conditions | Yield |
---|---|
In methanol at 80℃; for 2h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-pyridinecarboxylic acid, methyl ester With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; for 18h; Stage #2: With manganese(IV) oxide In dichloromethane at 20℃; for 2h; | 99% |
With bis-trimethylsilanyl peroxide; per-rhenic acid In dichloromethane; water at 24℃; for 6h; | 98% |
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 17h; | 98% |
4-pyridinecarboxylic acid, methyl ester
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With {Cp'2Th(μ-H)H}2 at 70℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With hydroxylamine In methanol at 20℃; for 72h; | 98% |
Stage #1: 4-pyridinecarboxylic acid, methyl ester With hydroxylamine hydrochloride; potassium hydroxide In methanol; water at 40℃; for 72h; Stage #2: With hydrogenchloride In methanol; water pH=5.5; | 93% |
With hydrogenchloride; methanol; hydroxylamine; sodium methylate |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Inert atmosphere; | 98% |
Stage #1: 4-pyridinecarboxylic acid, methyl ester With sodium tetrahydroborate In tetrahydrofuran at 70℃; for 0.25h; Stage #2: In tetrahydrofuran; methanol at 70℃; for 1h; | 52% |
With lithium aluminium tetrahydride In diethyl ether for 0.5h; | 38% |
Conditions | Yield |
---|---|
Stage #1: 4-pyridinecarboxylic acid, methyl ester With sodium hydroxide In toluene at 0℃; for 0.166667h; Stage #2: acetonitrile In toluene at 80℃; for 4h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 4-pyridinecarboxylic acid, methyl ester; α-bromoacetophenone In acetonitrile at 40℃; for 4h; Stage #2: methyl trifluoromethyl propiolate With N-ethyl-N,N-diisopropylamine In acetonitrile for 7h; | 98% |
4-pyridinecarboxylic acid, methyl ester
methyl iodide
4-(methoxycarbonyl)-1-methylpyridinium iodide
Conditions | Yield |
---|---|
In methanol | 97.2% |
Methylation; | 95% |
In dichloromethane at 30℃; | 87% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Glovebox; | 97% |
4-pyridinecarboxylic acid, methyl ester
2,2-difluoro-2-(4-methoxyphenyl)acetic acid
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 50℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Sealed tube; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
Stage #1: cobalt(II) sulphate heptahydrate; naphthalene-2-sulfonate In hexane at 40℃; for 0.5h; Stage #2: 4-pyridinecarboxylic acid, methyl ester; water In methanol; ethanol at 40℃; for 2h; | 96.6% |
4-pyridinecarboxylic acid, methyl ester
2,4-dinitrophenyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
In toluene for 16h; Reflux; | 96% |
In toluene for 48h; Reflux; | 25% |
4-pyridinecarboxylic acid, methyl ester
N-methylaniline
N-methyl-N-phenyl-4-pyridinecarboxamide
Conditions | Yield |
---|---|
With [(Me3Si)2N]3La(μ-Cl)Li(THF)3 In tetrahydrofuran at 30℃; for 0.333333h; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 70℃; for 0.00111111h; | 95.6% |
With hydrazine hydrate In ethanol at 20℃; for 3h; | 94.1% |
With hydrazine hydrate In ethanol at 23℃; for 16h; | 86% |
4-pyridinecarboxylic acid, methyl ester
trichloro(methyl isonicotinate)gold(III)
Conditions | Yield |
---|---|
In water KAuCl4*2H2O in H2O treated dropwise with stoich. amount of nitrogen donor base in H2O under stirring, pptd.; ppt. filtered off, washed (H2O) 3 times, dried (vac.), elem. anal.; | 95% |
4-pyridinecarboxylic acid, methyl ester
formamide
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; oxygen; sodium formate; silver nitrate at 80℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; regioselective reaction; | 95% |
With dipotassium peroxodisulfate; oxygen; sodium acetate; silver nitrate In water at 80℃; for 4h; Green chemistry; | 95% |
With iron(III) sulfate; sulfuric acid; dihydrogen peroxide at 10 - 20℃; for 8h; Temperature; | 80.4% |
Conditions | Yield |
---|---|
Stage #1: copper(ll) sulfate pentahydrate; isobutyric Acid In hexane at 39℃; for 0.583333h; Stage #2: 4-pyridinecarboxylic acid, methyl ester In methanol; ethanol; water at 39℃; for 2.16667h; | 95% |
4-pyridinecarboxylic acid, methyl ester
benzyl chloride
1-Benzyl-4-methoxycarbonyl-pyridinium; iodide
Conditions | Yield |
---|---|
In methanol for 24h; Heating; | 94% |
4-pyridinecarboxylic acid, methyl ester
1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
Conditions | Yield |
---|---|
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.; | 94% |
4-pyridinecarboxylic acid, methyl ester
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium
1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
Conditions | Yield |
---|---|
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.; | 94% |
4-pyridinecarboxylic acid, methyl ester
1-diphenylphosphinomethyl-1,2-dicarba-closo-dodecaborane
Conditions | Yield |
---|---|
In hexane Ar-atmosphere, to a stirred suspn. of Rh-compd. the pyridine-base is added,after 5-10 min. a soln. of the B-compd. added and the mixt. boiled for 1h; after cooling ppt. filtered off, washed with hexane and dried, elem. anal.; | 94% |
4-pyridinecarboxylic acid, methyl ester
cis-[Rh(CO)2Cl(methyl isonicotinate)]
Conditions | Yield |
---|---|
In dichloromethane (Rh(CO)2Cl)2 dissolved in CH2Cl2, methyl isonicotinate added, stirred atroom temp. for 10 min; evapn. under vac., washing (diethyl ether), elem. anal.; | 94% |
Conditions | Yield |
---|---|
Stage #1: 4-pyridinecarboxylic acid, methyl ester; 4-(bromoacetyl)toluene In acetonitrile at 40℃; for 4h; Stage #2: methyl trifluoromethyl propiolate With N-ethyl-N,N-diisopropylamine In acetonitrile for 7h; | 94% |
IUPAC Name: Methyl pyridine-4-carboxylate
Canonical SMILES: COC(=O)C1=CC=NC=C1
InChI: InChI=1S/C7H7NO2/c1-10-7(9)6-2-4-8-5-3-6/h2-5H,1H3
InChIKey: OLXYLDUSSBULGU-UHFFFAOYSA-N
Molecular Weight: 137.13598 [g/mol]
Molecular Formula: C7H7NO2
XLogP3: 0.9
H-Bond Donor: 0
H-Bond Acceptor: 3
EINECS: 219-546-8
storage temp. 2-8 °C
Appearance: clear orange to brown liquid
Melting Point: 8-8.5 °C(lit.)
Index of Refraction: 1.511
Molar Refractivity: 36.11 cm3
Molar Volume: 120.5 cm3
Surface Tension: 41.6 dyne/cm
Density: 1.137 g/cm3
Flash Point: 77.8 °C
Enthalpy of Vaporization: 44.13 kJ/mol
Boiling Point: 205.1 °C at 760 mmHg
Vapour Pressure: 0.255 mmHg at 25 °C
Product Categories of Methyl isonicotinate (CAS NO.2459-09-8): C7 and C8; Heterocyclic Building Blocks; Pyridines
Methyl isonicotinate (CAS NO.2459-09-8) is used for pharmaceutical intermediates.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 10
Hazard Note of Methyl isonicotinate (CAS NO.2459-09-8): Irritant
Methyl isonicotinate (CAS NO.2459-09-8), its Synonyms are 4-Methoxycarbonylpyridine ; Isonicotinic acid methyl ester ; Methyl 4-pyridinecarboxylate ; N-Methylisonicotinate ; Isonicotinic acid, methyl ester (8CI) .
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