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609-71-2

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609-71-2 Usage

Chemical Properties

White to light yellow powder

Uses

2-Hydroxynicotinic acid is used in chemical synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Definition

ChEBI: 2-Hydroxynicotinic acid is a member of pyridines and an aromatic carboxylic acid. It is a derivative of nicotinic acid, was found to exist in four polymorphs. It is used as a growth factor in Erwinia amylovora growth (pear and apple blossoms).

Check Digit Verification of cas no

The CAS Registry Mumber 609-71-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 9 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 609-71:
(5*6)+(4*0)+(3*9)+(2*7)+(1*1)=72
72 % 10 = 2
So 609-71-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO3/c8-5-4(6(9)10)2-1-3-7-5/h1-3H,(H,7,8)(H,9,10)/p-1

609-71-2 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (A15986)  2-Hydroxynicotinic acid, 98+%   

  • 609-71-2

  • 25g

  • 495.0CNY

  • Detail
  • Alfa Aesar

  • (A15986)  2-Hydroxynicotinic acid, 98+%   

  • 609-71-2

  • 100g

  • 1667.0CNY

  • Detail
  • Alfa Aesar

  • (A15986)  2-Hydroxynicotinic acid, 98+%   

  • 609-71-2

  • 500g

  • 6962.0CNY

  • Detail
  • Aldrich

  • (251054)  2-Hydroxypyridine-3-carboxylicacid  98%

  • 609-71-2

  • 251054-25G

  • 638.82CNY

  • Detail
  • Aldrich

  • (251054)  2-Hydroxypyridine-3-carboxylicacid  98%

  • 609-71-2

  • 251054-100G

  • 1,969.11CNY

  • Detail

609-71-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Hydroxynicotinic acid

1.2 Other means of identification

Product number -
Other names 2-hydroxy-3-nicotinic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:609-71-2 SDS

609-71-2Synthetic route

2-chloronicotinic acid
2942-59-8

2-chloronicotinic acid

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
3-bromo-pyridin-2-ol
13466-43-8

3-bromo-pyridin-2-ol

carbon dioxide
124-38-9

carbon dioxide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
2398-81-4

Nicotinic acid N-oxide

acetic anhydride
108-24-7

acetic anhydride

A

6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

B

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

C

3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide
111068-01-0

3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide

Conditions
ConditionsYield
for 6h; Heating;A 1.5%
B 5.4%
C 62%
Nicotinic acid N-oxide
2398-81-4

Nicotinic acid N-oxide

A

6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

B

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

C

3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide
111068-01-0

3-acetoxy-4-aza-3-methyl-1(3H)-isobenzofuranone 4-oxide

Conditions
ConditionsYield
With acetic anhydride for 6h; Heating;A 1.5%
B 5.4%
C 62%
2-chloronicotinic acid
2942-59-8

2-chloronicotinic acid

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

Conditions
ConditionsYield
With ammonium hydroxide at 155℃; for 20h;A n/a
B 60%
N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide
83164-33-4

N-(2,4-difluorophenyl)-2-(3-trifluoromethylphenoxy)-3-pyridinecarboxamide

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

3-Trifluoromethylphenol
98-17-9

3-Trifluoromethylphenol

C

2,4-difluorophenylamine
367-25-9

2,4-difluorophenylamine

D

N-(2,4-Difluorophenyl)-2-hydroxy-3-pyridinecarboxamide
130191-66-1

N-(2,4-Difluorophenyl)-2-hydroxy-3-pyridinecarboxamide

Conditions
ConditionsYield
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
2398-81-4

Nicotinic acid N-oxide

propionic acid anhydride
123-62-6

propionic acid anhydride

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

6-hydroxynicotinic acid

6-hydroxynicotinic acid

C

5-aza-3-methyl-4-propionyloxyisocoumarin
115147-79-0

5-aza-3-methyl-4-propionyloxyisocoumarin

D

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone 4-oxide

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone 4-oxide

Conditions
ConditionsYield
at 125℃; for 6h;A n/a
B n/a
C 12.9%
D 54.2%
Nicotinic acid N-oxide
2398-81-4

Nicotinic acid N-oxide

propionic acid anhydride
123-62-6

propionic acid anhydride

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

6-hydroxynicotinic acid

6-hydroxynicotinic acid

C

5-aza-3-methyl-4-propionyloxyisocoumarin
115147-79-0

5-aza-3-methyl-4-propionyloxyisocoumarin

D

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone
115147-80-3

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone

Conditions
ConditionsYield
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
2398-81-4

Nicotinic acid N-oxide

propionic acid anhydride
123-62-6

propionic acid anhydride

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

6-hydroxynicotinic acid

6-hydroxynicotinic acid

C

5-aza-3-methyl-4-propionyloxyisocoumarin
115147-79-0

5-aza-3-methyl-4-propionyloxyisocoumarin

D

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone
115147-80-3

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone

E

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone 4-oxide

4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone 4-oxide

F

4-aza-3-ethyl-3,5-dipropionyloxy-1(3H)-isobenzofuranone
115147-81-4

4-aza-3-ethyl-3,5-dipropionyloxy-1(3H)-isobenzofuranone

Conditions
ConditionsYield
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
504-29-0

2-aminopyridine

2-chloronicotinic acid
2942-59-8

2-chloronicotinic acid

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

2-hydroxy-nicotinic acid-[2]pyridylamide
99973-09-8

2-hydroxy-nicotinic acid-[2]pyridylamide

C

2-(2-hydroxy-nicotinoylimino)-2H-[1,2']bipyridyl-3'-carboxylic acid
109255-91-6

2-(2-hydroxy-nicotinoylimino)-2H-[1,2']bipyridyl-3'-carboxylic acid

Conditions
ConditionsYield
at 180 - 185℃;
2-hydroxy-3-cyanopyridine
20577-27-9

2-hydroxy-3-cyanopyridine

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With hydrogenchloride
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With hydrogenchloride
2-bromonicotinic acid
35905-85-2

2-bromonicotinic acid

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With potassium hydroxide; water at 180℃;
2-hydroxynicotinamide
10128-92-4

2-hydroxynicotinamide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

nicotinic acid
59-67-6

nicotinic acid

A

6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

B

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
91-22-5

quinoline

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

nicotinic acid
59-67-6

nicotinic acid

C

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

D

2-hydroxyquinoline
59-31-4

2-hydroxyquinoline

Conditions
ConditionsYield
With oxygen at 260 - 280℃; under 15751.3 - 64505.2 Torr; pH=7; Kinetics; Further Variations:; pH-values; Temperatures; Oxidation;
2-amino-pyridine-carboxylic acid-(3)

2-amino-pyridine-carboxylic acid-(3)

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite Diazotization;
hydrogenchloride
7647-01-0

hydrogenchloride

2-fluoronicotinic acid
393-55-5

2-fluoronicotinic acid

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

4-chloro-2-oxy-nicotinic acid

4-chloro-2-oxy-nicotinic acid

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With Pd-BaSO4; ethanol Hydrogenation;
6-oxy-pyridine-dicarboxylic acid-(2.5)

6-oxy-pyridine-dicarboxylic acid-(2.5)

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
With acetic anhydride; acetic acid at 210℃; im Rohr;
6--quinoline

6--quinoline

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

Quinoline-6-carboxylic acid
10349-57-2

Quinoline-6-carboxylic acid

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid
2-aminopyridine
504-29-0

2-aminopyridine

2-chloronicotinic acid
2942-59-8

2-chloronicotinic acid

A

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

B

2-hydroxy-nicotinic acid-[2]pyridylamide
99973-09-8

2-hydroxy-nicotinic acid-[2]pyridylamide

C

2-<2-hydroxy-nicotinoylimino>-2H-bipyridyl-3'-carboxylic acid

2-<2-hydroxy-nicotinoylimino>-2H-bipyridyl-3'-carboxylic acid

Conditions
ConditionsYield
at 180 - 185℃;
nicotinic acid
59-67-6

nicotinic acid

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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;
nicotinic acid
59-67-6

nicotinic acid

phenyl-β-pyridyl ketone

phenyl-β-pyridyl ketone

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
Nicotinic acid N-oxide
2398-81-4

Nicotinic acid N-oxide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
nicotinamide N-oxide
1986-81-8

nicotinamide N-oxide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PCl5; POCl3 / 115 - 120 °C
2: aqueous HCl
View Scheme
2-fluoronicotinamide
364-22-7

2-fluoronicotinamide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH3I / 80 °C / Behandeln des Reaktionsprodukts mit H2O
View Scheme
nicotinamide
98-92-0

nicotinamide

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
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
100921-66-2

bromo-2 butyl-3 pyridine

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KMnO4; H2O
2: KOH; H2O / 180 °C
View Scheme
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

2-Chloronicotinoyl chloride
49609-84-9

2-Chloronicotinoyl chloride

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

trimethylsilyl 2-(trimethylsilyloxy)nicotinate
183274-22-8

trimethylsilyl 2-(trimethylsilyloxy)nicotinate

Conditions
ConditionsYield
at 150℃; for 7h;100%
With chloro-trimethyl-silane In toluene Heating;
methanol
67-56-1

methanol

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

2-Hydroxy-nicotinic acid methyl ester; hydrochloride

2-Hydroxy-nicotinic acid methyl ester; hydrochloride

Conditions
ConditionsYield
With acetyl chloride at 0 - 20℃;100%
methanol
67-56-1

methanol

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile
10128-91-3

methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile

Conditions
ConditionsYield
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
67-56-1

methanol

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

methyl 2-oxo-1,2-dihydropyridine-3-carboxylate hydrochloride
203937-66-0

methyl 2-oxo-1,2-dihydropyridine-3-carboxylate hydrochloride

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

water
7732-18-5

water

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

diaquabis(2-hydroxynicotinato(1-))cobalt(II)
956331-98-9

diaquabis(2-hydroxynicotinato(1-))cobalt(II)

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

dichloro(2,2'-bipyridine)palladium(II)
14871-92-2

dichloro(2,2'-bipyridine)palladium(II)

[Pd bis(2-hydroxynicotinate)(2,2'-bipyridine)
503811-68-5

[Pd bis(2-hydroxynicotinate)(2,2'-bipyridine)

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

(2-Hydroxy-pyridin-3-yl)-imidazol-1-yl-methanone
211425-43-3

(2-Hydroxy-pyridin-3-yl)-imidazol-1-yl-methanone

Conditions
ConditionsYield
In tetrahydrofuran for 19h; Heating;98%
In tetrahydrofuran for 24h; Heating;
With Imidazole hydrochloride In tetrahydrofuran at 50℃; for 4h;
C20H15N2PS2
89430-08-0

C20H15N2PS2

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

2-thioxo-2,3-dihydro-4H-pyrido[3,2-e][1,3]oxazin-4-one

2-thioxo-2,3-dihydro-4H-pyrido[3,2-e][1,3]oxazin-4-one

Conditions
ConditionsYield
In dichloromethane97%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

5,5-dibenzyl-2,3,4,5-tetrahydropyridine
1416767-53-7

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
1416767-45-7

10,10-dibenzyl-8,9,10,10a-tetrahydrodipyrido[2,1-b:3',2'-e][1,3]oxazin-5(7H)-one

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

methyl iodide
74-88-4

methyl iodide

1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid
15506-18-0

1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

1,2-dihydro-1-(4-fluorobenzyl)-2-oxopyridine-3-carboxylic acid
66158-41-6

1,2-dihydro-1-(4-fluorobenzyl)-2-oxopyridine-3-carboxylic acid

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

5-chloro-2-hydroxypyridine-3-carboxylic acid
38076-80-1

5-chloro-2-hydroxypyridine-3-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium hypochlorite; chlorine; sodium hydrogensulfite In water; acetone95.6%
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
609-71-2

2-hydroxy-3-carboxypyridine

3-(hydroxymethyl)pyridin-2(1H)-one
42463-41-2

3-(hydroxymethyl)pyridin-2(1H)-one

Conditions
ConditionsYield
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
67-56-1

methanol

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

trans-bis(triphenylphosphine)palladium dichloride
28966-81-6

trans-bis(triphenylphosphine)palladium dichloride

trans-[PdCl(2-hydroxynicotinate)(PPh3)2

trans-[PdCl(2-hydroxynicotinate)(PPh3)2

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid
89960-36-1

1-benzyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

1-bromo-2-(triisopropylsilyl)acetylene
111409-79-1

1-bromo-2-(triisopropylsilyl)acetylene

2-hydroxy-4-((triisopropylsilyl)ethynyl)nicotinic acid

2-hydroxy-4-((triisopropylsilyl)ethynyl)nicotinic acid

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate at 90℃; for 14h;92%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

sodium molybdate dihydrate
7631-95-0

sodium molybdate dihydrate

water
7732-18-5

water

Na2[Mo2O4 bis(2-hydroxynicotinate)]*5H2O

Na2[Mo2O4 bis(2-hydroxynicotinate)]*5H2O

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

4-fluoroaniline
371-40-4

4-fluoroaniline

N-(4-fluorophenyl)-2-hydroxynicotinamide
951314-43-5

N-(4-fluorophenyl)-2-hydroxynicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;91%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

(2S)-2-phenylglycinol
20989-17-7

(2S)-2-phenylglycinol

2-hydroxy-N-[(1S)-2-hydroxy-1-phenylethyl]pyridine-3-carboxamide

2-hydroxy-N-[(1S)-2-hydroxy-1-phenylethyl]pyridine-3-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at -15 - 20℃; Inert atmosphere;90%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

diethylamine
109-89-7

diethylamine

2-hydroxy-N,N-diethylnicotinamide

2-hydroxy-N,N-diethylnicotinamide

Conditions
ConditionsYield
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%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

[RuCl2(η(6)-1,3,5-C6H3Me3)]2
52462-31-4

[RuCl2(η(6)-1,3,5-C6H3Me3)]2

chloroform
67-66-3

chloroform

[Ru(CH3)3C6H3(C6H3NO3)]2*1.5CHCl3

[Ru(CH3)3C6H3(C6H3NO3)]2*1.5CHCl3

Conditions
ConditionsYield
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%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

2-hydroxy-5-nitropyridine-3-carboxylic acid
6854-07-5

2-hydroxy-5-nitropyridine-3-carboxylic acid

Conditions
ConditionsYield
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 acid87%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

benzyl bromide
100-39-0

benzyl bromide

2-(Benzyloxy)nicotinic acid
14178-18-8

2-(Benzyloxy)nicotinic acid

Conditions
ConditionsYield
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
2038-03-1

4-(2-AMINOETHYL)MORPHOLINE

2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

2-hydroxy-N-(2-morpholinoethyl)nicotinamide
1221489-81-1

2-hydroxy-N-(2-morpholinoethyl)nicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;88%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorophenyl)-2-hydroxynicotinamide
951314-44-6

N-(4-chlorophenyl)-2-hydroxynicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;88%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

5-bromo-2-hydroxynicotinic acid
104612-36-4

5-bromo-2-hydroxynicotinic acid

Conditions
ConditionsYield
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 acid78%
2-hydroxy-3-carboxypyridine
609-71-2

2-hydroxy-3-carboxypyridine

dichloro(2,2'-bipyridine)platinum(II)
13965-31-6

dichloro(2,2'-bipyridine)platinum(II)

[PtCl(2-hydroxynicotinate)(2,2'-bipyridine)
503811-71-0

[PtCl(2-hydroxynicotinate)(2,2'-bipyridine)

Conditions
ConditionsYield
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
609-71-2

2-hydroxy-3-carboxypyridine

p-toluidine
106-49-0

p-toluidine

2-hydroxy-N-(p-tolyl)nicotinamide
72646-01-6

2-hydroxy-N-(p-tolyl)nicotinamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux;87%

609-71-2Relevant articles and documents

Synthesis, characterization and electrochemical investigations of mixed-ligand copper(II)-organic supramolecular frameworks

Singh, Sandeep K.,Srivastava, Ashish Kumar,Srivastava, Krishna,Banerjee, Rahul,Prasad, Jagdish

, p. 549 - 557 (2017)

Two mixed-ligand copper(II)-organic coordination compounds with 5,5′-dimethyl-2,2′-bipyridine (5,5′-Me2bpy) as a primary ligand while aliphatic malonate (Hmal) and aromatic 2-hydroxynicotinate (2-OHNA) as secondary ligands, were synthesized. These complexes are formulated as: [Cu(Hmal)(5,5′-Me2bpy)(H2O)](ClO4) 1 and [Cu2(2-OHNA)2(5,5′-Me2bpy)2(NO3)](NO3) 2. These two complexes were structurally characterized by single crystal X-ray diffraction analysis. Characterization was further supported by powder X-ray diffraction analysis, elemental analyses, FT-IR, FAB-MASS and TGA, DSC studies. Cyclic voltammetric and UV-visible spectral studies of these two complexes have also been done. The electrochemical studies of complex 1 in DMSO and DMF have shown that this complex undergoes quasi-reversible diffusion-controlled one-electron transfer reaction without any chemical complication while complex 2 in DMSO undergoes quasi-reversible diffusion-controlled one electron transfer reaction, following EC mechanism. The electrochemical behaviour of complex 2 in DMF is complicated probably due to presence of more than one species in solution phase.

A tautomeric ligand enables directed C-H hydroxylation with molecular oxygen

Li, Zhen,Wang, Zhen,Chekshin, Nikita,Qian, Shaoqun,Qiao, Jennifer X.,Cheng, Peter T.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan

, p. 1452 - 1457 (2021/06/30)

Hydroxylation of aryl carbon-hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/ pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from monoanionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon-hydrogen hydroxylation reaction. The conventional site selectivity dictated by heterocycles is overturned by this catalyst, thus allowing late-stage modification of compounds of pharmaceutical interest at previously inaccessible sites.

Halogen–metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate

Tian, Qingqiang,Shang, Suqin,Wang, Huajun,Shi, Guoqiang,Li, Zhiyao,Yuan, Jianyong

supporting information, (2017/12/05)

A selective and practical bromine–metal exchange on bromoheterocyclics bearing substituents with an acidic proton under non-cryogenic conditions was developed by a simple modification of an existing protocol. Our protocol of using a combination of i-PrMgCl and n-BuLi has not only solved the problem of intermolecular quenching that often occurred when using alkyl lithium alone as the reagent for halogen–lithium exchange, but also offered a highly selective method for performing bromo–metal exchange on dibrominated arene compounds through chelation effect.

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