4-chloropicolinic acid
diazomethyl-trimethyl-silane
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 4-chloropicolinic acid; diazomethyl-trimethyl-silane With methanol In tetrahydrofuran at 0 - 20℃; Stage #2: With acetic acid In tetrahydrofuran; methanol; water | 96% |
methanol
4-chloropicolinic acid
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 4-chloropicolinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Stage #2: methanol at 20℃; for 0.5h; | 92% |
Stage #1: 4-chloropicolinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1.5h; Stage #2: methanol at 20℃; for 0.5h; | 90% |
Stage #1: 4-chloropicolinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: methanol at 20℃; for 16h; | 74% |
2-Picolinic acid
methanol
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 2-Picolinic acid With thionyl chloride; N,N-dimethyl-formamide at 20 - 72℃; for 16.6667h; Stage #2: methanol at 20 - 55℃; for 0.75h; Stage #3: With water; sodium hydrogencarbonate In methanol at 45℃; pH=8 - 9; | 85% |
Stage #1: 2-Picolinic acid With thionyl chloride; sodium bromide In water; chlorobenzene for 16h; Reflux; Large scale; Stage #2: methanol In water; chlorobenzene; toluene for 1h; Reflux; Large scale; | 71% |
With thionyl chloride Heating / reflux; | 65% |
4-chloropicolinic acid
N,N-dimethyl-formamide
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With oxalyl dichloride In methanol; dichloromethane at 0 - 20℃; for 18h; | 74% |
methanol
4-chloro-pyridine-2-carbonyl chloride
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
at 20℃; for 0.5h; | 72% |
at 20 - 55℃; for 0.75h; | 39.6% |
2-Picolinic acid
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With sodium bromide In methanol; thionyl chloride; sodium hydrogencarbonate | 72% |
With sodium bromide In methanol; thionyl chloride; sodium hydrogencarbonate | 72% |
With thionyl chloride In ethyl acetate; N,N-dimethyl-formamide | 50% |
methanol
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 2-Picolinic acid With thionyl chloride at 20 - 100℃; for 157.333h; Stage #2: methanol at 0 - 20℃; for 18.5h; Stage #3: With sodium hydroxide In tetrahydrofuran; water; ethyl acetate | 65.2% |
Stage #1: 2-Picolinic acid With thionyl chloride at 80℃; for 72h; Stage #2: methanol at 0℃; for 1h; | 57% |
Stage #1: 2-Picolinic acid With thionyl chloride; N,N-dimethyl-formamide at 45 - 80℃; Stage #2: methanol In toluene at 0℃; for 1h; | 44% |
Stage #1: 2-Picolinic acid With thionyl chloride for 41h; Heating / reflux; Stage #2: methanol In diethyl ether at 0 - 20℃; for 1.5h; Stage #3: With sodium hydrogencarbonate In dichloromethane; water | 44% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride; sodium bromide for 16h; Reflux; | 57.9% |
pyridine-2-carbonyl chloride
methanol
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In toluene at 0℃; for 1h; | 33% |
at 0℃; for 0.75h; |
2-Picolinic acid
methanol
A
4-Chloro-pyridine-2-carboxylic acid methyl ester
B
methyl 4,6-dichloropyridine-2-carboxylate
Conditions | Yield |
---|---|
With thionyl chloride; sodium iodide 1.) 76 h, 2.) r.t., 0.5 h; Yield given. Multistep reaction. Yields of byproduct given; |
1-oxy-pyridine-2-carboxylic acid methyl ester
A
methyl 6-chloropicolinate
B
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With trichlorophosphate at 80℃; for 17h; Yield given. Yields of byproduct given; |
methyl pyridine-2-carboxylate
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: mCPBA / CH2Cl2 / 48 h / Ambient temperature 2: POCl3 / 17 h / 80 °C View Scheme |
4-chloropicolinic acid
methyl iodide
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 48h; |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 0℃; |
2-Picolinic acid
A
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride In methanol; water; toluene |
4-chloropicolinic acid
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 0 - 20 °C 2: 0.5 h / 20 °C View Scheme |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 20℃; | 100% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
methylamine
4-chloro-N-methylpicolinamide
Conditions | Yield |
---|---|
With magnesium chloride In tetrahydrofuran at 20℃; for 2.25h; | 98.5% |
In methanol at 0 - 5℃; for 2h; | 98% |
magnesium chloride In tetrahydrofuran at 20℃; for 2.25h; | 98.5% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
(4-chloropyridin-2-yl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; calcium chloride In tetrahydrofuran; methanol at 0℃; for 1h; | 98% |
With sodium tetrahydroborate; calcium chloride In tetrahydrofuran; methanol at 0℃; | 98% |
With methanol; sodium tetrahydroborate; calcium chloride In tetrahydrofuran at 20℃; Cooling with ice; Inert atmosphere; | 97% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
methyl-d3-amine hydrochloride
4-chloropyridinyl-2-(N-1',1',1'-trideuteromethylcarboxamide)
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 33℃; for 15h; Temperature; Time; Solvent; Inert atmosphere; Large scale; | 98% |
With potassium carbonate In tetrahydrofuran at 20℃; for 20h; | 96% |
With potassium carbonate In tetrahydrofuran at 20℃; for 20h; | 96% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-chloropicolinamide
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 15 - 30℃; Solvent; Temperature; | 92.6% |
With ammonium hydroxide | 88% |
With ammonia In methanol; water for 0.166667h; | 85% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-chloro-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 2h; Stage #2: With methanol; Rochelle's salt In tetrahydrofuran at -78 - 20℃; for 1h; | 91% |
With diisobutylaluminium hydride In tetrahydrofuran; toluene at -70℃; for 1h; | 74% |
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; calcium chloride / methanol; tetrahydrofuran / 1.5 h / 0 °C 2: selenium(IV) oxide / 1,4-dioxane / 4 h / 95 °C View Scheme | |
Multi-step reaction with 2 steps 1: calcium chloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 0 °C 2: manganese(IV) oxide / chloroform / 2.5 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: methanol; calcium chloride; sodium tetrahydroborate / tetrahydrofuran / 20 °C / Cooling with ice; Inert atmosphere 2: manganese(IV) oxide / chloroform / 36 h / 80 °C / Inert atmosphere View Scheme |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Cyclopropylamine
N-cyclopropyl-4-chloro-2-pyridinecarboxamide
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 2 - 20℃; | 90.1% |
In tetrahydrofuran | |
In tetrahydrofuran |
4-Chloro-pyridine-2-carboxylic acid methyl ester
N-(5-nitropyridin-2-yl)-4-thiocyanatothiazol-2-amine
methyl 4-(2-(5-nitropyridin-2-ylamino)thiazol-4-ylthio)picolinate
Conditions | Yield |
---|---|
With potassium phosphate; diothiothreitol In methanol; N,N-dimethyl-formamide at 23℃; | 90% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-iodo-2-nicotinic acid
Conditions | Yield |
---|---|
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With hydrogen iodide; hypophosphorous acid In water at 85 - 107℃; Stage #2: With sodium hydroxide In water at 20 - 95℃; for 1h; | 89% |
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With hydrogen iodide; hypophosphorous acid at 85 - 107℃; Stage #2: With water; sodium hydroxide at 20 - 95℃; for 1h; | 89% |
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With hydrogen iodide; hypophosphorous acid In water at 85 - 107℃; Stage #2: With sodium hydroxide; water at 20 - 95℃; for 1.5h; | 66% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-amino-phenol
methyl 4‐(4‐aminophenoxy)picolinate
Conditions | Yield |
---|---|
Stage #1: 4-amino-phenol With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 4-Chloro-pyridine-2-carboxylic acid methyl ester With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere; | 89% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
C15H22ClN3O3
Conditions | Yield |
---|---|
With magnesium chloride In tetrahydrofuran at 20℃; for 2h; | 88% |
With magnesium chloride In tetrahydrofuran at 20℃; for 2h; | 76% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-methoxycarbonylphenylboronic acid
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In toluene at 110℃; for 48h; Inert atmosphere; | 88% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
4-chloropicolinic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 1h; | 87% |
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With methanol; sodium hydroxide; water at 20℃; for 0.25h; Stage #2: With hydrogenchloride; water pH=2; | |
Stage #1: 4-Chloro-pyridine-2-carboxylic acid methyl ester With methanol; sodium hydroxide; water at 0 - 20℃; for 0.25h; Stage #2: With hydrogenchloride; water pH=2; |
4-Chloro-pyridine-2-carboxylic acid methyl ester
cyclohexylamine
4-chloro-N-cyclohexylpyridine-2-carboxamide
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 2 - 20℃; | 84.6% |
In tetrahydrofuran | |
In tetrahydrofuran |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 6h; | 84% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
2-(2-Aminoethoxy)ethanol
C10H13ClN2O3
Conditions | Yield |
---|---|
In tetrahydrofuran at 70℃; for 2h; Reflux; | 84% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
N-butylamine
N-butyl-4-chloropicolinamide
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 2 - 20℃; | 82.9% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
sodium cyclopropylsulfinate
methyl 4-(cyclopropylsulfonyl)picolinate
Conditions | Yield |
---|---|
With quinoline; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 140℃; for 0.166667h; Microwave irradiation; | 82% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
5-hydroxypentylamine
C11H15ClN2O2
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; Reflux; | 81% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With silver(II) fluoride In acetonitrile at 20℃; Inert atmosphere; Autoclave; | 80% |
With silver(II) fluoride In acetonitrile at 20℃; for 1h; Mechanism; | 72% |
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran; diethyl ether at -45 - 25℃; for 4h; Inert atmosphere; | 78% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
aniline
4-chloro-N-phenylpyridine-2-carboxamide
Conditions | Yield |
---|---|
With trimethylaluminum In n-heptane; dichloromethane for 24h; Heating; | 77% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
sodium 4-methylbenzenesulfinate
methyl 4-tosylpicolinate
Conditions | Yield |
---|---|
With quinoline; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 140℃; for 0.166667h; Microwave irradiation; | 75% |
4-Chloro-pyridine-2-carboxylic acid methyl ester
1,5-diaminopentane
C11H16ClN3O
Conditions | Yield |
---|---|
In tetrahydrofuran at 70℃; for 5h; Reflux; | 73% |
Product Name: Methyl 4-chloropicolinate (CAS NO.24484-93-3)
Molecular Formula: C7H6ClNO2
Molecular Weight: 171.58g/mol
Mol File: 24484-93-3.mol
Appearance: Brown Solid
Boiling point: 264 °C at 760 mmHg
Flash Point: 113.5 °C
Density: 1.294 g/cm3
Index of Refraction: 1.531
Molar Refractivity: 41.01 cm3
Molar Volume: 132.5 cm3
Surface Tension: 44.4 dyne/cm
Enthalpy of Vaporization: 50.18 kJ/mol
Vapour Pressure: 0.00997 mmHg at 25°C
XLogP3-AA: 1.7
H-Bond Donor: 0
H-Bond Acceptor: 3
Structure Descriptors of Methyl 4-chloropicolinate (CAS NO.24484-93-3):
IUPAC Name: methyl 4-chloropyridine-2-carboxylate
Canonical SMILES: COC(=O)C1=NC=CC(=C1)Cl
InChI: InChI=1S/C7H6ClNO2/c1-11-7(10)6-4-5(8)2-3-9-6/h2-4H,1H3
InChIKey: VTENWIPSWAMPKI-UHFFFAOYSA-N
Product Categories: blocks; Carboxes; Pyridines; Acids and Derivatives; Heterocycles; pharmacetical; Pyridine; Aromatics Compounds; Aromatics; Bases & Related Reagents; Nucleotides; Pharmaceutical intermediate; Picolinic acid series
Safety Information of Methyl 4-chloropicolinate (CAS NO.24484-93-3):
Hazard Codes: Xi
Hazard Note: Irritant
HazardClass: IRRITANT
Methyl 4-chloropicolinate , its CAS NO. is 24484-93-3, the synonyms are Methyl 4-chloropyridine-2-carboxylate ; 4-Chloropyridine-2-carboxylic acid methyl ester .
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