98-98-6

Basic information

• Product Name: Picolinic acid
• Synonyms: Picolinic acid, 99% 25GR;2-PYRIDINECARBOXYLIC ACID FOR SYNTHESIS;Picolinic aci;Picolinic acid, 2-Carboxypyridine;2-Picolinic acid ReagentPlus(R), 99%;2- picolinate;2-Picolinic acid Vetec(TM) reagent grade, 98%;PCL 016
• CAS NO: 98-98-6
• Molecular Formula: C₆H₅NO₂
• Molecular Weight: 123.11
• EINECS: 202-719-7
• Product Categories: C6 to C7;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines;carboxylic acid;Nitrogen cyclic compounds;Pyridine;Organic acids;API intermediates;Pyridine series;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 98-98-6.mol
• Article Data: 157

Chemical Properties

• Melting Point: 139-142 °C(lit.)
• Boiling Point: 229.19°C (rough estimate)
• Flash Point: 139°(232°F)
• Appearance: White to almost white/Crystalline Powder
• Density: 1.3147 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5423 (estimate)
• Storage Temp.: Store at RT.
• Solubility: H2O: 50 mg/mL, clear
• PKA: 1.07(at 25℃)
• Water Solubility: 887 g/L (20 ºC)
• Merck: 14,7403
• BRN: 109595
• CAS DataBase Reference: Picolinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Picolinic acid(98-98-6)
• EPA Substance Registry System: Picolinic acid(98-98-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-36/37/38
• Safety Statements: 26-36-33-24/25
• WGK Germany: 3
• RTECS: TJ7344000
• TSCA: Yes
• Hazardous Substances Data: 98-98-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-white to tan powder. easily soluble in glacial acetic acid, almost insoluble in ether, chloroform and carbon disulfide.

Uses

2-Picolinic acid is used as a chelate for alkaline earth metals. It is also used to prepare picolinato ligated transition metal complexes. In synthetic organic chemistry, has been used as a substrate in the Mitsunobu reaction and in the Hammick reaction.

Application

2-Picolinic acid is used in the preparation of 2-Aminodihydro[1,3]thiazines as BACE 2 inhibitors and their preparation and use in the treatment of diabetes.Metal complexes of picolinic acid were prepared by the refluxion of metal salts and picolinic acid in ethanol taking 1:3 molar ratio for 6 hours. The solutions were concentrated and cooled, to crystallize out the complexes.The complexes were washed with ether to remove the excess ligand.

Definition

ChEBI: Picolinic acid is a pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan. It has a role as a MALDI matrix material and a human metabolite. It is a conjugate acid of a picolinate.

Synthesis

2-Picolinic acid synthesis: In a 500ml three-necked flask, add 100g of 2-cyanopyridine and 200g of deionized water, then start stirring, heat up to 50°C, add 128.2g of 30% sodium hydroxide to the flask, after adding, add Continue to heat up, react under reflux for 4 hours, then distill water, after 50 g of distilled water, cool the reaction solution to 20°C, add 30% hydrochloric acid, adjust the pH value of the reaction solution to 2.5, then turn on the steam to heat up the water and steam to the kettle When the temperature reaches 120°C, the reaction solution is evaporated to dryness, and the distilled water is completed. Then, 300 g of anhydrous alcohol is added dropwise to the flask to maintain the temperature of the reaction solution at 55°C. After cooling and crystallization, a solid was precipitated, filtered and dried to obtain 106.0 g of 2-picolinic acid with a yield of 89.6%.

Purification Methods

Crystallise the acid from water or *benzene. The picrate has m 185-187o (from MeOH). [Beilstein 22 H 33, 22 I 502, 22 II 30, 22 III/IV 303, 22/2 V 3.]

InChI:InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)/p-1

Synthetic route

2-Hydroxymethylpyridine (586-98-1) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;	98%
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 0.5h; Green chemistry;	97%
Stage #1: 2-Hydroxymethylpyridine With sodium hydroxide; Rh(trop2NH)(PPh3)(OTf); water; cyclohexanone at 25℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride; water chemoselective reaction;	96%

1-(pyridine-2-yl)ethanol (20988-55-0, 18728-61-5, 27911-63-3, 59042-90-9) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium hydroxide In dimethyl sulfoxide at 130℃; under 3000.3 Torr; for 12h; Autoclave;	79%

2-Cyanopyridine (100-70-9) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With potassium phosphate buffer at 30℃; for 144h; Rhodococcus sp. AJ270 cells;	46.3%
With phosphate buffer at 30℃; for 144h; rhodococcus rhodocrous AJ270, pH 7.0;	30%
With acetic acid tert-butyl ester; sulfuric acid In acetic acid at 45℃; for 0.1h; Ritter reaction; In flow;

C16H17NO2 (1309453-54-0) → 2-Picolinic acid (98-98-6) + C16H15NO2 (338415-92-2) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
Stage #1: C16H17NO2 With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: With hydrogenchloride In water	A 18% B 84% C 18%

α-picoline (109-06-8) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With sulfuric acid; ozone; acetic acid; manganese(II) acetate at 16℃; for 1h;	97%
Stage #1: α-picoline With β‐cyclodextrin In water at 60℃; for 0.5h; Stage #2: With sulfuric acid; dihydrogen peroxide; boric acid In water at 40℃; for 6h;	89.3%
With potassium hydroxide; oxygen; 18-crown-6 ether In 1,2-dimethoxyethane at 25℃; for 96h;	85%

pyridine-2-carbaldehyde (1121-60-4) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water at 20℃; for 12h; Temperature; Enzymatic reaction;	99%
With 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3-a]pyridinium chloride; dihydrogen peroxide In water; tert-butyl alcohol at 20℃; for 2h;	96%
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	95%

C15H14ClNO (1309453-49-3) → 2-Picolinic acid (98-98-6) + C15H12ClNO (1309453-57-3) + para-chlorobenzoic acid (74-11-3)

Conditions	Yield
Stage #1: C15H14ClNO With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 10h; Stage #2: With hydrogenchloride In water	A 51% B 45% C 51%

pyridine-2-carbaldehyde (1121-60-4) → 2-Hydroxymethylpyridine (586-98-1) + 2-Picolinic acid (98-98-6)

Conditions	Yield
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;	A 47% B 47%
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 7h; Cannizzaro reaction;	A 39% B 36%

4-Chloropyridine (626-61-9) + 2-oxo-propionic acid ethyl ester (617-35-6) + ferrous(II) sulfate heptahydrate → 2-Picolinic acid (98-98-6)

Conditions	Yield
With sodium hydroxide; sulfuric acid; dihydrogen peroxide In water; toluene	50%

4-Chloropyridine (626-61-9) + 2-oxo-propionic acid ethyl ester (617-35-6) + ferrous(II) sulfate heptahydrate + conc. H2 SO4 → 2-Picolinic acid (98-98-6)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water; toluene	50%

2-pyridinecarboxylic acid N-oxide (824-40-8) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;	88%
With triphenylphosphine; [MoO2Cl2(dmf)2] In tetrahydrofuran for 2h; Heating;	81%

α-picoline (109-06-8) + N-hydroxyphthalimide (524-38-9) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With acetic acid	77%

2-(Bromomethyl)pyridine (55401-97-3) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With 5,10,15,20-tetra(4-nitrophenyl) porphyrinato iron chloride; [bis(acetoxy)iodo]benzene; water In methanol at 50℃; for 12h;	89%

2-iodopyridine (5029-67-4) + carbon monoxide (201230-82-2) → 2-Picolinic acid (98-98-6)

Conditions	Yield
Stage #1: 2-iodopyridine; carbon monoxide With potassium carbonate In water at 100℃; under 3750.38 Torr; for 15h; Autoclave; Stage #2: With hydrogenchloride In water	37%
With water; sodium carbonate; palladium diacetate at 20 - 165℃; under 10501.1 - 22502.3 Torr; for 0.333333h; microwave irradiation;	15%

2-Hydroxymethylpyridine (586-98-1) → pyridine-2-carbaldehyde (1121-60-4) + 2-Picolinic acid (98-98-6)

Conditions	Yield
With tert.-butylhydroperoxide; [O-Cu4(triethanolamine)4(BOH)4][BF4]2 In acetonitrile at 69.84℃; for 6h; Title compound not separated from byproducts.;
With copper(ll) sulfate pentahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-(4-fluorophenyl)-1-(pyroll-2-yl)methanimine; dihydrogen peroxide; potassium carbonate In water at 60℃; for 1h;
With sodium hypochlorite In 1,2-dimethoxyethane; water at 20℃; for 4h;	A 52 %Chromat. B 43 %Chromat.

carbon dioxide (124-38-9) + pyridin-2-yl sulfurofluoridate (127827-58-1) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;

2,2'-Pyridil (492-73-9) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With tetraethylammonium bromide; potassium oxide In N,N-dimethyl-formamide at 30℃; for 3.5h;	59%
With 6-(pyridin-2-yl)-6,7-dihydrobenzo[g]naphtho[2,3-c](5,8,13,14-tetraone)cinnolinyl; triethylamine In methanol at 20℃; for 30h;

2-chloropyridine (109-09-1) + dinorbornyl phosphine + palladium bis(benzonitrile) dichloride → 2-Picolinic acid (98-98-6)

Conditions	Yield
With sodium carbonate In ethanol; water

α-picoline (109-06-8) + N-hydroxyphthalimide (524-38-9) + acetylacetonatocobalt(II) Co(AA)2 → 2-Picolinic acid (98-98-6)

Conditions	Yield
With acetic acid In water; benzonitrile

indolin-1-yl(pyridin-2-yl)methanone (864424-24-8) → 2-Picolinic acid (98-98-6) + 1-indoline (496-15-1)

Conditions	Yield
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h;	A n/a B 95%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + pyridin-2-yl 2,3,4,5,6-pentafluorobenzenesulfonate → 2-Picolinic acid (98-98-6)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	78%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + pyridin-2-yl trifluoromethanesulfonate (65007-00-3) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;	75%

2-bromo-pyridine (109-04-6) + carbon dioxide (124-38-9) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;	78%

N-(4-(1H-pyrazol-1-yl)naphthalen-1-yl)picolinamide → 2-Picolinic acid (98-98-6) + 4-(1H-pyrazol-1-yl)naphthalen-1-amine

Conditions	Yield
With sodium hydroxide In ethanol at 90℃; for 8h;
With sodium hydroxide In ethanol at 100℃; for 12h; Schlenk technique;

p-nitrophenyl picolinate (74104-89-5) → 2-Picolinic acid (98-98-6) + p-nitrophenolate (14609-74-6)

Conditions	Yield
With C18H12Cl2Cu2N2O6 at 25℃; pH=7.9; Kinetics; Concentration; pH-value; Reagent/catalyst;
With sodium hydroxide In water; acetonitrile at 25℃; Kinetics; Mechanism;

pyridine-2-carboxylic acid N-tert-butylamide (71653-50-4) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With sodium hydroxide

2-Cyanopyridine (100-70-9) → 2-Picolinic acid (98-98-6) + pyridine-2-carboxylic acid amide (1452-77-3)

Conditions	Yield
Stage #1: 2-Cyanopyridine With Br(1-)*C24H30N4Rh(1+); water In isopropyl alcohol at 25℃; for 0.5h; Inert atmosphere; Stage #2: With potassium tert-butylate In isopropyl alcohol at 25℃; for 2h; Inert atmosphere;	A 48% B 52%

2-bromo-pyridine (109-04-6) + potassium formate (590-29-4) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;	53%

Clopyralid (1702-17-6) → 2-Picolinic acid (98-98-6)

Conditions	Yield
With Graphite; sodium hydroxide In water at 25℃; for 3h; Reagent/catalyst; Electrolysis;

Clopyralid (1702-17-6) → 2-Picolinic acid (98-98-6) + 3-chloropyridine-2-carboxylic acid (57266-69-0)

Conditions	Yield
With Graphite; sodium hydroxide In water at 25℃; for 3h; Electrolysis;
With Graphite; sodium hydroxide In water at 25℃; for 6h; pH=11.5 - 13.5; Reagent/catalyst; pH-value; Electrolysis;

2-Picolinic acid (98-98-6) → pyridine-2-carbonyl chloride (29745-44-6)

Conditions	Yield
With thionyl chloride In neat (no solvent) at 20℃; for 48h; Inert atmosphere;	100%
With thionyl chloride In benzene at 0℃; for 12h; Reflux;	60%
With thionyl chloride

2-Picolinic acid (98-98-6) → pipecolic Acid (4043-87-2)

Conditions	Yield
With (R)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine; hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate In methanol at 60℃; under 75006 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; ratio;	100%
With hydrogen; platinum(IV) oxide In ethanol at 125℃; under 18751.5 Torr; for 1h; Irradiation; microwave irradiation;	99%
With hydrogen; platinum(IV) oxide In ethanol at 80℃; under 5171.62 Torr; for 0.166667h; microwave irradiation;	99%

2-Picolinic acid (98-98-6) → pyridine-2-carboxylic anhydride (16837-39-1)

Conditions	Yield
Stage #1: 2-Picolinic acid With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; Stage #2: With bis(trichloromethyl) carbonate In tetrahydrofuran at 0 - 20℃;	100%
With 1-ethyl-piperidine; Phenyl N-methyl-N-phenylphosphoramidochloridate In dichloromethane for 0.5h; Ambient temperature;
With 1-ethyl-piperidine; N,N'-diphenylphosphorodiamidic chloride In dichloromethane for 0.5h; Ambient temperature;
With 2,4,6-trimethyl-pyridine; bis(trichloromethyl) carbonate In tetrahydrofuran for 0.0166667h;

2-Picolinic acid (98-98-6) → 4-chloro-pyridine-2-carbonyl chloride (53750-66-6)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 12h;	100%
With thionyl chloride; N,N-dimethyl-formamide at 50℃; for 17.5h; Reflux;	100%
With thionyl chloride; sodium bromide at 80℃; for 22h;	98%

2-Picolinic acid (98-98-6) + rac-methylbenzylamine (618-36-0) → pyridine-2-carboxylic acid (1-phenyl-ethyl)amide (2909-32-2)

Conditions	Yield
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h;	100%
With dmap In dichloromethane at 20℃; for 1h;	93%
With pyridine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	73%

piperidine (110-89-4) + 2-Picolinic acid (98-98-6) → 2-(N,N-penta-1,5-diyl-carboxamido)-pyridine (340004-68-4)

Conditions	Yield
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h;	100%
Stage #1: 2-Picolinic acid With iodine; triethylamine; phosphorous acid trimethyl ester In dichloromethane for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: piperidine In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice;	85%
With dmap In dichloromethane at 20℃; for 1h;	82%

2-Picolinic acid (98-98-6) + 3-Phenylpropan-1-amine (2038-57-5) → N-(3-phenylpropyl)picolinamide

Conditions	Yield
With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h;	100%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	91%
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane at 20℃;

2-Picolinic acid (98-98-6) + 3-hydroxypyridine-2-carboxamide (933-90-4) → N-(3-hydroxypicolinoyl)picolinamide (1394853-33-8)

Conditions	Yield
Stage #1: 2-Picolinic acid With dmap; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 3-hydroxypyridine-2-carboxamide at 20℃; for 73h; Reflux; Inert atmosphere;	100%

2-Picolinic acid (98-98-6) + C14H18O → 1-(1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Cooling with ice;	100%

2-Picolinic acid (98-98-6) + C15H20O → 1-(4'-methyl-1,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)ethyl picolinate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Cooling with ice;	100%

2-Picolinic acid (98-98-6) + C25H34N2O → C31H37N3O2

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	100%

2-Picolinic acid (98-98-6) + ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (156626-44-7) → ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-α-L-rhamnopyranoside

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2.5h;	100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	91%

2-Picolinic acid (98-98-6) + 2-amino-6-(1,1-dimethylethyl)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid methyl ester (213192-26-8) → methyl 6-(tert-butyl)-2-(picolinamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Conditions	Yield
With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile at 60℃; for 20h;	100%

pyridine-2-carbaldehyde (1121-60-4) + 2-Picolinic acid (98-98-6) + diphenyltin(IV) oxide (2273-51-0) + 2-amino-phenol (95-55-6) → [(OC6H4NCHC5H4N)Sn(NC5H4CO2)(C6H5)2] (1187857-43-7)

Conditions	Yield
In benzene soln. of Sn oxide and picolinic acid in C6H6 was added to soln. of aldehyde and phenol; refluxed for 40 min; concd. (vac.); filtered; elem. anal.;	99.5%

2-Picolinic acid (98-98-6) + benzylamine (100-46-9) → N-benzyl-2-pyridinecarboxamide (18904-38-6)

Conditions	Yield
With tetrachloromethane; Bis(p-nitrophenyl) phosphate; 3-Methyl-1-phenyl-2-phospholene 1-oxide In toluene at 110℃; for 20h; Green chemistry;	99%
Stage #1: 2-Picolinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: benzylamine With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	98%
Stage #1: 2-Picolinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; Stage #2: benzylamine With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	98%

2-Picolinic acid (98-98-6) + L-tryptophan methyl ester (4299-70-1) → (S)-methyl3-(1H-indol-3-yl)-2-(picolinamido)propanoat (934745-79-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h; Inert atmosphere;	99%
Stage #1: 2-Picolinic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: L-tryptophan methyl ester at 20℃; for 12h;	90%
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	82%
With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane 2 h, 0 deg C, 2 h, 20 deg C;

2-Picolinic acid (98-98-6) + 2-amino-4-methylbenzophenone (4937-62-6) → 4-methyl-2-(picolinoylamino)benzophenone

Conditions	Yield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 40 - 50℃;	99%

2-Picolinic acid (98-98-6) + (2S,3S)-1,4-bis(phenylmethoxy)-2,3-diaminobutane (109582-31-2, 136597-79-0, 139951-77-2, 142071-04-3) → (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-pyridinoylamino)butane (890662-56-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃;	99%

2-Picolinic acid (98-98-6) + sodium chloride (7647-14-5) + palladium dichloride → [Pd(picolinic acid)2] (22602-40-0)

Conditions	Yield
In water to aq. soln. Na2(PdCl4), prepared in situ by react. PdCl2 and NaCl, was added pyridine-2-carboxylic acid in water and stirred for 2 h; ppt. was filtered, washed with water and acetone, and dried in vacuo; elem. anal.;	99%

2-Picolinic acid (98-98-6) + mercury(II) diacetate (1600-27-7) → mercuric pyridine-2-carboxylate

Conditions	Yield
In methanol mixing MeOH (or EtOH) solns. of stoich. amts. of Hg(OAc)2 and carboxylic acid; elem. anal.;	99%

2-Picolinic acid (98-98-6) + thallium(I) carbonate → thallium(I) pyridine-2-carboxylate (86668-74-8)

Conditions	Yield
In methanol stoich. amts., refluxing for 30-45 min; cooling to -15°C, filtration, pptn. on standing;	99%
In methanol N2-atmosphere;

2-Picolinic acid (98-98-6) + bis[2-(2,4-difluorophenyl)pyridinato-N,C6']iridium(III) chloride dimer → iridium(III) bis[2-(4,6-difluorophenyl)pyridinato]picolinate (376367-93-0)

Conditions	Yield
With Na2CO3 In not given Ir-complex reacted with ligand in the presence of Na2CO3;	99%
With sodium carbonate In 1,2-dimethoxyethane for 9h; Inert atmosphere; Reflux;	91%
With sodium carbonate In 1,2-dimethoxyethane at 85℃; for 9h; Inert atmosphere;	91%
With Na2CO3 In 2-ethoxy-ethanol soln. Ir complex, ligand and Na2CO3 in 2-ethoxyethanol was refluxed for 24 h; solvent was roto-evapd., residue was chromed. on silica (CH2Cl2 - n-hexane);	75%

2-Picolinic acid (98-98-6) + 1,1’-bi-2-naphthol (18531-99-2, 602-09-5, 18531-94-7) + tri-n-propyl borate (688-71-1) → C26H16BNO4 (866128-44-1, 866239-74-9)

Conditions	Yield
In toluene binaphthol mixed with B-compd. in dry toluene under Ar, refluxed with constant stirring at <=90°C, cooled to 60-70°C after 8h, dried picolinic acid added, refluxed for several hours; filtered, washed with toluene and methanol, dried in vac.,;	99%

2-Picolinic acid (98-98-6) + 5-(4-methoxybenzyloxy)pent-3-yn-2-ol (124222-34-0) → 5-(4-methoxybenzyloxy)-3-pentyn-2-yl pyridine-2-carboxylate (1189125-38-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;	99%

2-Picolinic acid (98-98-6) + C14H18O (175439-34-6, 194152-65-3, 896465-30-8) → 2-(4-phenylcyclohexylidene)ethyl picolinate (1240401-98-2)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;	99%

2-Picolinic acid (98-98-6) + C20H29NO3 → 2-(2-hexyl-1-(phenoxycarbonyl)piperidin-4-ylidene)ethyl picolinate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Cooling with ice;	99%

2-Picolinic acid (98-98-6) + (S)-methyl 2-amino-4,4-dimethylpentanoate hydrochloride (79777-81-4) → C14H20N2O3 (1353864-05-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

2-Picolinic acid (98-98-6) + palladium dichloride + 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → C33H40ClN3O2Pd

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Reflux;	99%
With caesium carbonate In 1,4-dioxane at 80℃; for 20h; Schlenk technique; Inert atmosphere;	65%

2-Picolinic acid (98-98-6) + (R,E)-2-(3-phenylpropylidene)cyclopentan-1-ol → (R,E)-2-(3-phenylpropylidene)cyclopentyl picolinate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Cooling with ice;	99%

Upstream product

• 109-06-8 α-picoline 
• 109-04-6 2-bromo-pyridine 
• 100-70-9 2-Cyanopyridine 
• 1008-89-5 2-phenylpyridine 
• 4377-37-1 2-trichloromethylpyridine 
• 2196-95-4 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide 
• 91-63-4 2-methylquinoline 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 118-48-9 isatoic anhydride 
• 17281-71-9 pyridinium bis(ethoxycarbonyl)methylide 
• 26838-86-8 pyridine-2-carboxylic acid phenyl ester 
• 21802-37-9 (E)-4-methoxy-2,2'-bipyridine-6-carbaldehyde oxime 
• 783334-77-0 2-hydroxymuconic 6-semialdehyde 
• 492-73-9 2,2'-Pyridil 

Downstream Products

• 2459-07-6 methyl pyridine-2-carboxylate 
• 100714-45-2 N-(4-(dimethylamino)phenyl)picolinamide 
• 14888-39-2 4'-ethoxy-(pyridin-2-yl)carboxanilide 
• 41727-18-8 1-(pyridin-2-yl)cyclohexanol 
• 29263-67-0 α-(4-methylphenyl)-2-pyridinemethanol 
• 27652-89-7 (4-chlorophenyl)-2-pyridylmethanol 
• 197512-40-6 1-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-ol 
• 27693-37-4 (3-nitrophenyl)(pyridin-2-yl)methanone 
• 71653-37-7 pyridine-2-carboxylic acid benzyl ester 
• 31796-72-2 phenyl(2-pyridinyl)methanol 
• 1752-86-9 N-(p-tolyl)picolinamide 
• 27805-39-6 (4-methoxyphenyl)(pyridin-2-yl)methanol 
• 27693-42-1 (3,4-dimethoxyphenyl)(pyridin-2-yl)methanone 
• 31749-10-7 (3,4-dimethoxyphenyl)(pyridin-2-yl)methanol 

Relevant articles and documents

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ANODIC OXIDATION OF 2-PICOLINE

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