Conditions | Yield |
---|---|
With hydrogenchloride; water for 6h; Heating; | 92% |
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 110℃; for 48h; Inert atmosphere; | 63% |
Heating; | |
With sodium hydroxide In ethanol; water |
Conditions | Yield |
---|---|
Stage #1: 3-bromo-pyridin-2-ol With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #3: carbon dioxide In tetrahydrofuran; hexane at -20℃; for 0.5h; | 79% |
Nicotinic acid N-oxide
acetic anhydride
A
6-hydroxy-3-pyridinecarboxylic acid
B
2-hydroxy-3-carboxypyridine
C
3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide
Conditions | Yield |
---|---|
for 6h; Heating; | A 1.5% B 5.4% C 62% |
Nicotinic acid N-oxide
A
6-hydroxy-3-pyridinecarboxylic acid
B
2-hydroxy-3-carboxypyridine
C
3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide
Conditions | Yield |
---|---|
With acetic anhydride for 6h; Heating; | A 1.5% B 5.4% C 62% |
2-chloronicotinic acid
A
2-hydroxy-3-carboxypyridine
B
2-aminopyridin-3-carboxylic acid
Conditions | Yield |
---|---|
With ammonium hydroxide at 155℃; for 20h; | A n/a B 60% |
N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide
A
2-hydroxy-3-carboxypyridine
B
3-Trifluoromethylphenol
C
2,4-difluorophenylamine
D
N-(2,4-Difluorophenyl)-2-hydroxy-3-pyridinecarboxamide
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water for 48h; Heating; | A 57% B n/a C n/a D 28% |
With hydrogenchloride; acetic acid In water for 48h; Product distribution; Mechanism; Heating; | A 57% B n/a C n/a D 28% |
Nicotinic acid N-oxide
propionic acid anhydride
A
2-hydroxy-3-carboxypyridine
C
5-aza-3-methyl-4-propionyloxyisocoumarin
Conditions | Yield |
---|---|
at 125℃; for 6h; | A n/a B n/a C 12.9% D 54.2% |
Nicotinic acid N-oxide
propionic acid anhydride
A
2-hydroxy-3-carboxypyridine
C
5-aza-3-methyl-4-propionyloxyisocoumarin
D
4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone
Conditions | Yield |
---|---|
at 160℃; for 4h; Yield given. Further byproducts given; | A n/a B n/a C 39.8% D 16.4% |
Nicotinic acid N-oxide
propionic acid anhydride
A
2-hydroxy-3-carboxypyridine
C
5-aza-3-methyl-4-propionyloxyisocoumarin
D
4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone
F
4-aza-3-ethyl-3,5-dipropionyloxy-1(3H)-isobenzofuranone
Conditions | Yield |
---|---|
at 160℃; for 4h; Product distribution; Mechanism; various temperatures and times; | A n/a B n/a C 39.8% D 16.4% E 8.3% F 2.1% |
2-aminopyridine
2-chloronicotinic acid
A
2-hydroxy-3-carboxypyridine
B
2-hydroxy-nicotinic acid-[2]pyridylamide
C
2-(2-hydroxy-nicotinoylimino)-2H-[1,2']bipyridyl-3'-carboxylic acid
Conditions | Yield |
---|---|
at 180 - 185℃; |
2-hydroxy-3-cyanopyridine
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride |
2-bromonicotinic acid
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With potassium hydroxide; water at 180℃; |
2-hydroxynicotinamide
2-hydroxy-3-carboxypyridine
nicotinic acid
A
6-hydroxy-3-pyridinecarboxylic acid
B
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With potassium hydroxide; fluorine In water at 0℃; for 3.5h; Yield given. Yields of byproduct given; | |
With potassium hydroxide; fluorine In water at 0℃; Yield given. Yields of byproduct given; | |
With water; oxygen Quantum yield; Further Variations:; pH-values; Reagents; Irradiation; |
quinoline
A
3-pyridinecarboxaldehyde
B
nicotinic acid
C
2-hydroxy-3-carboxypyridine
D
2-hydroxyquinoline
Conditions | Yield |
---|---|
With oxygen at 260 - 280℃; under 15751.3 - 64505.2 Torr; pH=7; Kinetics; Further Variations:; pH-values; Temperatures; Oxidation; |
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite Diazotization; |
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With Pd-BaSO4; ethanol Hydrogenation; |
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
With acetic anhydride; acetic acid at 210℃; im Rohr; |
A
2-hydroxy-3-carboxypyridine
B
Quinoline-6-carboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate; sulfuric acid |
2-aminopyridine
2-chloronicotinic acid
A
2-hydroxy-3-carboxypyridine
B
2-hydroxy-nicotinic acid-[2]pyridylamide
Conditions | Yield |
---|---|
at 180 - 185℃; |
Conditions | Yield |
---|---|
With sulfuric acid; quinolinium dichromate(VI); acetic acid at 50℃; for 24h; Kinetics; | |
With sulfuric acid; quinolinium dichromate(VI); acetic acid In water at 49.85℃; for 48h; Kinetics; Further Variations:; Solvents; Temperatures; | |
With quinolinium dichromate In water; acetic acid at 49.84℃; for 48h; Kinetics; Mechanism; Solvent; Temperature; Inert atmosphere; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / 30percent H2O2 / acetic acid / 3 h / 90 °C 2: PCl5, POCl3 3: conc. NH4OH / 20 h / 155 °C View Scheme | |
Multi-step reaction with 3 steps 1: 80 percent / 30percent H2O2 / acetic acid / 3 h / 90 °C 2: 65 percent / POCl3, Et3N / 4 h / 100 °C 3: conc. NH4OH / 20 h / 155 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PCl5, POCl3 2: conc. NH4OH / 20 h / 155 °C View Scheme | |
Multi-step reaction with 2 steps 1: 65 percent / POCl3, Et3N / 4 h / 100 °C 2: conc. NH4OH / 20 h / 155 °C View Scheme | |
Multi-step reaction with 2 steps 1: POCl3 / dimethylformamide 2: Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: PCl5; POCl3 / 115 - 120 °C 2: aqueous HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH3I / 80 °C / Behandeln des Reaktionsprodukts mit H2O View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous H2O2; acetic acid 2: PCl5; POCl3 / 115 - 120 °C 3: aqueous HCl View Scheme |
bromo-2 butyl-3 pyridine
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KMnO4; H2O 2: KOH; H2O / 180 °C View Scheme |
2-hydroxy-3-carboxypyridine
2-Chloronicotinoyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | 100% |
With phosphorus pentachloride anschliessendes Erwaermen; | |
With phosphorus pentachloride anschliessendes Erwaermen; |
2-hydroxy-3-carboxypyridine
1,1,1,3,3,3-hexamethyl-disilazane
trimethylsilyl 2-(trimethylsilyloxy)nicotinate
Conditions | Yield |
---|---|
at 150℃; for 7h; | 100% |
With chloro-trimethyl-silane In toluene Heating; |
Conditions | Yield |
---|---|
With acetyl chloride at 0 - 20℃; | 100% |
methanol
2-hydroxy-3-carboxypyridine
methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With sulfuric acid Heating / reflux; | 100% |
Stage #1: 2-hydroxy-3-carboxypyridine With thionyl chloride In dichloromethane at 0℃; Stage #2: In tetrahydrofuran; dichloromethane at 20℃; Stage #3: methanol In tetrahydrofuran; dichloromethane at 20℃; | 81.8% |
With sulfuric acid In toluene Dean-Stark; Reflux; | 74% |
methanol
2-hydroxy-3-carboxypyridine
methyl 2-oxo-1,2-dihydropyridine-3-carboxylate hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-3-carboxypyridine With thionyl chloride In tetrahydrofuran; dichloromethane at 20℃; for 1h; Stage #2: methanol In tetrahydrofuran; dichloromethane at 20℃; | 100% |
2-hydroxy-3-carboxypyridine
water
cobalt(II) diacetate tetrahydrate
diaquabis(2-hydroxynicotinato(1-))cobalt(II)
Conditions | Yield |
---|---|
With aq. ammonia In water soln. of ligand in H2O added to soln. of Co salt in H2O; pH adjusted to 8 (a few drops of concd. ammonia soln.); stored for a few d; filtered; ppt. washed with H2O; dried in dessicator over NaOH; elem. anal.; | 100% |
2-hydroxy-3-carboxypyridine
dichloro(2,2'-bipyridine)palladium(II)
[Pd bis(2-hydroxynicotinate)(2,2'-bipyridine)
Conditions | Yield |
---|---|
With triethylamine In methanol; ethanol stirred suspn. of Pd complex in methanol mixed with methanolic suspn. ofligand and triethylamine, stirred for 1 day; sentrifuged, washed with ethanol, dried (silica gel); elem. anal.; | 99% |
2-hydroxy-3-carboxypyridine
1,1'-carbonyldiimidazole
(2-Hydroxy-pyridin-3-yl)-imidazol-1-yl-methanone
Conditions | Yield |
---|---|
In tetrahydrofuran for 19h; Heating; | 98% |
In tetrahydrofuran for 24h; Heating; | |
With Imidazole hydrochloride In tetrahydrofuran at 50℃; for 4h; |
C20H15N2PS2
2-hydroxy-3-carboxypyridine
Conditions | Yield |
---|---|
In dichloromethane | 97% |
2-hydroxy-3-carboxypyridine
5,5-dibenzyl-2,3,4,5-tetrahydropyridine
10,10-dibenzyl-8,9,10,10a-tetrahydrodipyrido[2,1-b:3',2'-e][1,3]oxazin-5(7H)-one
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; Inert atmosphere; | 97% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; | 97% |
2-hydroxy-3-carboxypyridine
methyl iodide
1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water for 2h; Methylation; Heating; | 96% |
With potassium hydroxide In methanol; water for 12h; Reflux; Inert atmosphere; | 65% |
With potassium hydroxide In methanol; water at 0 - 80℃; for 16h; | 45% |
2-hydroxy-3-carboxypyridine
1-chloromethyl-4-fluorobenzene
1,2-dihydro-1-(4-fluorobenzyl)-2-oxopyridine-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-3-carboxypyridine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 1-chloromethyl-4-fluorobenzene In N,N-dimethyl-formamide at 50℃; for 12h; Stage #3: With sodium hydroxide In water for 4h; Reflux; | 96% |
2-hydroxy-3-carboxypyridine
5-chloro-2-hydroxypyridine-3-carboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium hypochlorite; chlorine; sodium hydrogensulfite In water; acetone | 95.6% |
With sodium hydroxide; chlorine In water at 0 - 35℃; | 84% |
Stage #1: 2-hydroxy-3-carboxypyridine With sodium hydroxide; sodium hypochlorite In water at 20℃; for 48h; Stage #2: With sodium sulfite In water at 20℃; for 0.5h; | 78% |
2-hydroxy-3-carboxypyridine
3-(hydroxymethyl)pyridin-2(1H)-one
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-3-carboxypyridine With chloro-trimethyl-silane; 1,1,1,2,2,2-hexamethyldisilane In toluene at 110℃; for 0.5h; Stage #2: With diisobutylaluminium hydride In dichloromethane; toluene at -40 - 20℃; Stage #3: With hydrogenchloride; water In dichloromethane; toluene at -10℃; pH=4; | 95% |
Stage #1: 2-hydroxy-3-carboxypyridine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 2h; Heating / reflux; Stage #2: With diisobutylaluminium hydride In toluene at -78℃; for 4h; Stage #3: With methanol In toluene | 59% |
methanol
2-hydroxy-3-carboxypyridine
trans-bis(triphenylphosphine)palladium dichloride
Conditions | Yield |
---|---|
With triethylamine In methanol; ethanol stirred suspn. of Pd complex mixed with methanolic suspn. of ligand and triethylamine, stirred for 1 week; centrifuged, washed with ethanol, dried (silica gel); elem. anal., XRD; | 94% |
2-hydroxy-3-carboxypyridine
benzyl bromide
1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water for 8.5h; Heating; | 93% |
With potassium hydroxide In methanol; water for 12h; Reflux; Inert atmosphere; | 71% |
Stage #1: 2-hydroxy-3-carboxypyridine With potassium hydroxide In methanol; water for 0.25h; Heating / reflux; Stage #2: benzyl bromide In methanol; water for 1.5h; Heating / reflux; Stage #3: With hydrogenchloride; water | 55% |
2-hydroxy-3-carboxypyridine
1-bromo-2-(triisopropylsilyl)acetylene
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate at 90℃; for 14h; | 92% |
Conditions | Yield |
---|---|
In water ligand added to soln. of Mo salt, suspn. refluxed for 6 h; filtered, washed with water, dried (silica gel); | 91% |
2-hydroxy-3-carboxypyridine
4-fluoroaniline
N-(4-fluorophenyl)-2-hydroxynicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 91% |
2-hydroxy-3-carboxypyridine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at -15 - 20℃; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-3-carboxypyridine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 70℃; for 24h; Stage #2: diethylamine In tetrahydrofuran at 70℃; for 18h; | 90% |
Stage #1: 2-hydroxy-3-carboxypyridine With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; Stage #2: diethylamine In tetrahydrofuran at 60℃; for 2h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With NaOMe In methanol byproducts: NaCl; suspn. of Ru-complex and ligand in MeOH was stirred at room temp. for 10min, soln. of NaOMe in MeOH was added, stirred for 30 min under N2; solvent was evapd. under reduced pressure, extd. with CH2Cl2, hexane wasadded, solvent was evapd.; elem. anal.; | 89% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0 - 50℃; for 4h; | 88% |
With sulfuric acid; nitric acid 1.) RT, 16 h, 2.) from 50 deg C to 70 deg C, 1.5 h; | 87% |
With sulfuric acid; nitric acid | 87% |
Conditions | Yield |
---|---|
With n-Bu4POH In tetrahydrofuran; water at 0 - 20℃; | 88% |
Stage #1: 2-hydroxy-3-carboxypyridine; benzyl bromide With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Stage #2: With sodium hydroxide Inert atmosphere; |
4-(2-AMINOETHYL)MORPHOLINE
2-hydroxy-3-carboxypyridine
2-hydroxy-N-(2-morpholinoethyl)nicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 88% |
2-hydroxy-3-carboxypyridine
4-chloro-aniline
N-(4-chlorophenyl)-2-hydroxynicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 88% |
2-hydroxy-3-carboxypyridine
5-bromo-2-hydroxynicotinic acid
Conditions | Yield |
---|---|
Stage #1: With sodium hydroxide; bromine In water at 0℃; for 0.0833333h; Stage #2: 2-hydroxy-3-carboxypyridine With sodium hydroxide In water at 50℃; for 44h; Stage #3: With hydrogenchloride In water at 0℃; pH=2; | 87% |
With sodium hydroxide; bromine at 0 - 50℃; for 18h; | 78% |
With bromine In water; acetic acid | 78% |
2-hydroxy-3-carboxypyridine
dichloro(2,2'-bipyridine)platinum(II)
[PtCl(2-hydroxynicotinate)(2,2'-bipyridine)
Conditions | Yield |
---|---|
With triethylamine In methanol; ethanol stirred suspn. of Pt complex in methanol mixed with methanolic suspn. ofligand and triethylamine, stirred for 2 weeks; sentrifuged, washed with ethanol, dried (silica gel); elem. anal.; | 87% |
2-hydroxy-3-carboxypyridine
p-toluidine
2-hydroxy-N-(p-tolyl)nicotinamide
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 87% |
Molecular Structure of 2-Hydroxynicotinic acid (CAS NO. 609-71-2):
IUPAC Name: 2-Oxo-1H-pyridine-3-carboxylic acid
Molecular Formula: C6H5NO3
Molecular Weight: 139.108800 g/mol
Index of Refraction: 1.579
Molar Refractivity: 31.84 cm3
Molar Volume: 95.8 cm3
Surface Tension: 61 dyne/cm
Density: 1.451 g/cm3
Flash Point: 217.5 °C
Enthalpy of Vaporization: 75.92 kJ/mol
Boiling Point: 436 °C at 760 mmHg
Vapour Pressure: 8.03E-09 mmHg at 25 °C
Melting Point: 258-261 °C(lit.)
BRN: 119028
EINECS: 210-198-2
Product Categories: blocks;Carboxes;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Organic acids;CHIRAL CHEMICALS
Safety Information of 2-Hydroxynicotinic acid (CAS NO. 609-71-2):
Hazard Codes: Xi
Hazard Note: Irritant
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
S37/39:Wear suitable gloves and eye/face protection
WGK Germany: 3
HazardClass: IRRITANT
2-Hydroxynicotinic acid with cas registry number of 609-71-2 is also called NSC 226152 ; 1,2-Dihydro-2-oxo-3-pyridinecarboxylic acid ; 1,2-Dihydro-2-oxonicotinic acid .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View