100-54-9

Usage

Uses

Used in Chemical Synthesis:
3-Cyanopyridine is used as a key intermediate in the preparation of arylthiazolines and arylimidazolines via dibromodimethylhydantoin-catalyzed condensation of aryl nitriles with ethylene diamine or aminoethanethiol. This application is particularly relevant in the field of organic chemistry, where these compounds can be further utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
3-Cyanopyridine is used as a building block in the synthesis of various pharmaceutical compounds. Its unique structure allows for the formation of diverse chemical entities with potential therapeutic applications. The versatility of 3-cyanopyridine makes it a valuable component in the development of new drugs and drug candidates.
Used in Agrochemical Industry:
In addition to its applications in the pharmaceutical industry, 3-cyanopyridine is also utilized in the agrochemical sector. It serves as a precursor for the synthesis of various agrochemicals, including pesticides and herbicides. The use of 3-cyanopyridine in this industry contributes to the development of more effective and targeted crop protection products.
Overall, 3-cyanopyridine is a versatile chemical intermediate with applications in various industries, including pharmaceuticals, agrochemicals, and organic chemistry. Its unique properties and reactivity make it an essential component in the synthesis of a wide range of compounds with potential applications in healthcare, agriculture, and other fields.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2155, 1988 DOI: 10.1016/S0040-4039(00)86697-6

Shipping

UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).

Purification Methods

It is recrystallised to constant melting point from o-xylene/hexane. [Beilstein 22/2 V 115.]

InChI:InChI:1S/C6H4N2/c7-4-6-2-1-3-8-5-6/h1-3,5H

Synthetic route

nicotinamide (98-92-0) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; copper(l) chloride In toluene at 100℃; for 24h;	99%
With 3 A molecular sieve at 150 - 500℃; under 0.001 Torr; for 0.666667h; Pyrolysis;	98%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h;	96%

3-pyridinecarboxaldehyde (500-22-1) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;	99%
With ammonia; oxygen In ethanol; water for 1.5h; Reflux;	94%
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride at 100℃; for 1h;	92%

3-hydroxymethylpyridin (100-55-0) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
Stage #1: 3-hydroxymethylpyridin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;	99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure;	99%
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;	91%

3-iodopyridine (1120-90-7) + sodium cyanide (773837-37-9) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;	99%

3-Methylpyridine (108-99-6) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With manganese; ammonia; oxygen; pyrographite at 335℃; Temperature;	98.7%
With ammonia In water at 200 - 300℃; Concentration;	97%
With aluminum oxide; ammonia; oxygen at 300℃; Concentration; Temperature;	93.1%

3-Bromopyridine (626-55-1) + potassium hexacyanoferrate(II) trihydrate → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;	98%

thionicotinamide (4621-66-3) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With tellurium tetrachloride; triethylamine In chloroform for 3h; Ambient temperature;	96%
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;	95%
With bis(tri-n-butyltin)oxide In benzene for 0.5h; Heating;	92%

3-pyridinealdoxime (1193-92-6) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;	95%
With 1,4-diaza-bicyclo[2.2.2]octane; trichlorophosphate In dichloromethane at 20℃; for 0.0833333h;	94%
With aluminium trichloride; sodium iodide In acetonitrile for 2.5h; Heating;	92%

3-iodopyridine (1120-90-7) + potassium cyanide (151-50-8) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With tributyltin chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 22℃; for 3h;	95%

3-Chloropyridine (626-60-8) + potassium ferrocyanide → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one; Hexadecane at 160℃; for 16h;	95%
With sodium carbonate; cyclopalladated ferrocenylimine tricyclohexylphosphine In 1-methyl-pyrrolidin-2-one at 140℃; for 18h;	82%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;	57%
With tetra(adamantyl)biphosphine; palladium diacetate; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 16h; Inert atmosphere;	66 %Chromat.

zinc(II) cyanide (557-21-1) + pyridin-3-yl sulfurofluoridate → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; zinc In N,N-dimethyl-formamide at 80℃; for 3h; Reagent/catalyst; Concentration; Temperature; Solvent; Inert atmosphere;	95%

3-iodopyridine (1120-90-7) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 5h;	94%

3-Bromopyridine (626-55-1) + potassium cyanide (151-50-8) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With tributyltin chloride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;	93%
With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 16h;	88%
With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 16h; Product distribution; other heteroaromatic halides, var. solv., temp., also NaCN; selective reactivity of var. heteroaromatic halides;
dibromobis(triphenylphosphine)nickel(II) In acetonitrile at 60℃; for 8h;

3-Aminomethylpyridine (3731-52-0) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With aluminum oxide In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;	93%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;	92%
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In dichloromethane at 20℃; for 12h; Oxidation;	90%

2-(pyridin-3-yl)-1,3,4-oxadiazole (65943-95-5) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 8h;	93%

3-iodopyridine (1120-90-7) + potassium ferrocyanide → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;	90%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Catalytic behavior;	90%

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide (119986-58-2) + 3-pyridylboronic acid (1692-25-7) → pyridine-3-carbonitrile (100-54-9) + 4-methyl-N-(4-chlorophenyl)benzenesulfonamide (2903-34-6)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 17h; Catalytic behavior; Reflux;	A 92% B n/a

3-Bromopyridine (626-55-1) + potassium ferrocyanide → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 18h; Inert atmosphere;	91%
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 8h; Inert atmosphere; Sealed tube;	91%
With 5,5’-(1,2-phenylene)bis(1H-tetrazole); copper(I) iodide; caesium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	90%

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide + 3-pyridylboronic acid (1692-25-7) → pyridine-3-carbonitrile (100-54-9) + 4-nitro-N-(4-chlorophenyl)benzenesulfonamide (16937-03-4)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 11h; Catalytic behavior; Reflux;	A 91% B n/a

nicotinic acid (59-67-6) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With ammonium carbonate; diphosphorus tetraiodide In carbon disulfide at 20℃; for 5h;	90%
With hydroxyammonium sulfate; zinc for 0.416667h; Microwave irradiation;	89%
With aluminum oxide; aminosulfonic acid; urea for 0.2h; Irradiation;	77%

3-Aminomethylpyridine (3731-52-0) → pyridine-3-carbonitrile (100-54-9) + nicotinamide (98-92-0)

Conditions	Yield
With water; oxygen at 140℃; under 3800.26 Torr; for 24h;	A n/a B 90%
With ammonia; oxygen; vanadia at 375℃; Product distribution; other catalysts, effect of the presence of O2;
With ammonia In 1,4-dioxane; water at 130℃; under 4560.31 Torr; for 3h; Autoclave;	A 7 %Chromat. B 84 %Chromat.

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide + 3-pyridylboronic acid (1692-25-7) → pyridine-3-carbonitrile (100-54-9) + 4-bromo-benzenesulfonic acid-(4-chloro-anilide) (6295-97-2)

Conditions	Yield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux;	A 90% B n/a

3-Picolyl chloride (3099-31-8) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With sodium azide; tris(o-methoxyphenyl)phosphine; palladium dichloride In acetone at 70℃; for 36h; Schlenk technique;	89%
With sodium azide; palladium diacetate; XPhos In acetone at 80℃; for 12h; Inert atmosphere;	70%

3-Bromopyridine (626-55-1) + dicyanozinc (557-21-1) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 0.0333333h; Substitution; microwave irradiation;	88%
With 1,1'-bis-(diphenylphosphino)ferrocene; zinc diacetate; zinc; tris(dibenzylideneacetone)dipalladium (0) In water; N,N-dimethyl-formamide at 90 - 100℃; for 3h;	80%
With water; tri tert-butylphosphoniumtetrafluoroborate; zinc; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	40%
With bromine; triphenylphosphine; zinc; palladium on activated charcoal In dimethyl amine at 80℃; for 5h;	75 % Chromat.
With bromine; triphenylphosphine; zinc; palladium on activated charcoal In N,N-dimethyl acetamide at 80℃; for 5h;	75 % Chromat.

nicotinaldehyde oxime (51892-16-1) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve In acetonitrile at 80℃; for 1h;	88%
With palladium diacetate; triphenylphosphine In acetonitrile for 7h; Reflux;	87%
With per-rhenic acid In water; 1,3,5-trimethyl-benzene for 72h; Heating;	84%
With per-rhenic acid In water; 1,3,5-trimethyl-benzene for 3h; Heating;	84%
With N,N-dimethyl-formamide at 135℃; for 48h;	83%

3-Bromopyridine (626-55-1) + zinc(II) cyanide (557-21-1) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 100℃; for 12h; Inert atmosphere;	88%

C13H13N3 → pyridine-3-carbonitrile (100-54-9) + N-methylaniline (100-61-8)

Conditions	Yield
With bis(trimethylsilyl)amide yttrium(III) In toluene at 20℃; for 12h; Inert atmosphere;	A 87% B n/a

3-Bromopyridine (626-55-1) + N-cyanoimidazole (36289-36-8) → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; cyanation;	86%

3-Bromopyridine (626-55-1) + K4[Fe(CN)6] → pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
With sodium carbonate; palladium diacetate at 140℃; for 16h;	86%
With sodium carbonate; potassium iodide; N,N`-dimethylethylenediamine; copper(II) bis(tetrafluoroborate) In N,N-dimethyl acetamide at 140℃; for 16h;	67%
With sodium carbonate; palladium diacetate at 140℃; for 16h;
With palladium diacetate; sodium carbonate In N,N-dimethyl acetamide at 120℃; for 8h;	86 % Chromat.

pyridine-3-carbonitrile (100-54-9) → nicotinamide oxime (1594-58-7)

Conditions	Yield
With hydroxylamine hydrochloride; sodium methylate In methanol Heating;	100%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In isopropyl alcohol at 80 - 85℃;	91%
With hydroxylamine hydrochloride In ethanol for 8h; Reflux;	89%

pyridine-3-carbonitrile (100-54-9) → nicotinamide (98-92-0)

Conditions	Yield
With manganese(IV) oxide; silica gel In hexane for 8h; Heating;	100%
With manganese(IV) oxide; silica gel In chlorobenzene for 5h; Heating;	100%
With water at 30℃; for 5.5h; Large scale reaction; Enzymatic reaction;	99%

pyridine-3-carbonitrile (100-54-9) + trifluoromethylsulfonic anhydride (358-23-6) + cyclohepta[b]furan-2(2H)-one (4481-35-0) → C16H9F3N2O4S

Conditions	Yield
In dichloromethane at 20℃;	100%

pyridine-3-carbonitrile (100-54-9) → (pyridin-3-yl)methylamine hydrochloride (84359-15-9)

Conditions	Yield
With hydrogenchloride; hydrogen In 1,4-dioxane; methanol at 60℃; under 375.038 Torr; for 18h; Flow reactor;	100%
Stage #1: pyridine-3-carbonitrile With hydrogen at 130℃; under 750.075 Torr; for 6h; Stage #2: Acidic conditions; chemoselective reaction;	99%
With fac-[(CO)3Mn(iPr2P(CH2)2PiPr2)(triflato)]; potassium tert-butylate; hydrogen In iso-butanol at 110℃; under 25858.1 Torr; for 0.25h; Catalytic behavior; Glovebox; Schlenk technique; Inert atmosphere; Autoclave;	96%

pyridine-3-carbonitrile (100-54-9) → 3-pyridinecarboxaldehyde (500-22-1)

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; High pressure; Green chemistry;	99.9%
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;	96%
Stage #1: pyridine-3-carbonitrile With diisobutylaluminium hydride In toluene at 20℃; for 0.222222h; Flow reactor; Stage #2: With water; sodium L-tartrate In toluene at 0℃; chemoselective reaction;	52%

pyridine-3-carbonitrile (100-54-9) → 3-Aminomethylpyridine (3731-52-0)

Conditions	Yield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;	99.9%
With palladium 10% on activated carbon; ammonia; hydrogen In methanol at 30℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Temperature; Pressure; Autoclave;	93.44%
With hydrogen; silica gel; nickel In methanol; ammonia at 120℃; under 7600 Torr; for 6h;	86%

pyridine-3-carbonitrile (100-54-9) → 3-cyanopyridine N-oxide (14906-64-0)

Conditions	Yield
With dihydrogen peroxide; VxSi4xO6.4x In acetonitrile at 80℃; for 3h;	99%
With phosphomolybdic acid; dihydrogen peroxide In water at 50 - 65℃; for 3h;	98%
With titanium silicate; dihydrogen peroxide In methanol at 60℃; for 25h; Oxidation;	97.3%

pyridine-3-carbonitrile (100-54-9) + silver tetrafluoroborate (14104-20-2) + silver trifluoroacetate (2966-50-9) + silver(I) ethynediide → (Ag2C2)(AgCF3CO2)8(3-pyCONH2)2(H2O)4

Conditions	Yield
In water High Pressure; excess moistened Ag2C2 was added to concd. aq. soln. CF3COOAg anf AgBF4,soln. was filtered, 3-cyanopyridine was added, suspn. was placed in Tef lon-lined stainless steel reaction vessel and heated at 108°C for40 h; react. mixt was cooled to room temp. (6°C/h); elem. anal.;	99%

pyridine-3-carbonitrile (100-54-9) + iron(II) perchlorate hexahydrate + sodium dicyanamide (1934-75-4) → [Fe(dicyanamide)2(3-cyanopyridine)2]n

Conditions	Yield
In methanol; water; acetonitrile powder X-ray diffraction;	99%
In methanol; water; acetonitrile soln. 3-CNpy and Na(N(CN)2) in MeCN-MeOH was heated for 5 min, aq. soln.Fe(ClO4)2*6H2O was added; soln. was filtered and left to stand at room temp. for 3 weeks; elem. anal.;	15%

pyridine-3-carbonitrile (100-54-9) + 4-(N,N-dimethylamino)phenylmagnesium bromide lithium chloride complex → 4-(4-(dimethylamino)phenyl)nicotinonitrile (1428419-75-3)

Conditions	Yield
Stage #1: pyridine-3-carbonitrile With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: 4-(N,N-dimethylamino)phenylmagnesium bromide lithium chloride complex In tetrahydrofuran at -30℃; for 2h; Inert atmosphere; Stage #3: With chloranil In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; regioselective reaction;	99%

pyridine-3-carbonitrile (100-54-9) + 1-bromo-octane (111-83-1) → 4-octylnicotinonitrile (1428419-53-7)

Conditions	Yield
Stage #1: pyridine-3-carbonitrile With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: 1-bromo-octane With tert-butylmagnesium chloride; magnesium; lithium chloride; zinc(II) chloride In tetrahydrofuran at -50 - 25℃; for 1h; Inert atmosphere; Stage #3: With chloranil In tetrahydrofuran at 20℃; Inert atmosphere; regioselective reaction;	99%

pyridine-3-carbonitrile (100-54-9) + 2-methylbenzyl bromide (89-92-9) → 3-cyano-1-(2-methylbenzyl)pyridin-1-ium bromide

Conditions	Yield
In acetonitrile at 80℃;	99%

pyridine-3-carbonitrile (100-54-9) + 4-amino-6-methyl-3-oxo-2,3,4,5-tetrahydro-1,2,4-triazine hydrochloride → Pymetrozine

Conditions	Yield
With hydrogen; Raney nickel In methanol; water	98.6%

pyridine-3-carbonitrile (100-54-9) → thionicotinamide (4621-66-3)

Conditions	Yield
With diammonium sulfide In methanol at 80℃; for 0.25h; microwave irradiation;	98%
With hydrogenchloride; thiophosphate sodium salt hydrate In water; water-d2 at 50℃; for 24h; pH=6.5; Sealed tube;	97%
With diammonium sulfide In methanol at 20℃; for 18h;	96.4%

pyridine-3-carbonitrile (100-54-9) + benzyl bromide (100-39-0) → N-benzyl-3-cyanopyridin-1-ium bromide (6516-53-6)

Conditions	Yield
In acetonitrile for 18h; Reflux;	98%
In acetonitrile at 80℃;	96%
In nitrobenzene at 40℃; Rate constant;

pyridine-3-carbonitrile (100-54-9) + 2-amino-4,5-dimethyl-3-thiophenecarboxylic acid ethyl ester (4815-24-1) → 5,6-dimethyl-2-(pyridin-3-yl)thieno[2,3-d]pyrimidin-4(3H)-one

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 0℃; for 10h; Heating;	98%
With hydrogenchloride In 1,4-dioxane for 5h;	66%

pyridine-3-carbonitrile (100-54-9) → 3-(1H-tetrazol-5-yl)pyridine (3250-74-6)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide for 24h; Reflux;	98%
With sodium azide In N,N-dimethyl-formamide at 110 - 120℃; for 24h;	98%
With sodium azide; 1-ethyl-3-methylimidazolium hydrogensulfate at 100℃; for 9h;	96%

pyridine-3-carbonitrile (100-54-9) + 1-amino-2-propene (107-11-9) → N-allylnicotinamide (98952-82-0)

Conditions	Yield
With Iron(III) nitrate nonahydrate at 125℃; for 24h; Neat (no solvent); Sealed tube;	98%

pyridine-3-carbonitrile (100-54-9) + propan-1-ol-3-amine (156-87-6) → 2-(pyridin-3-yl)-5,6-dihydro-4H-1,3-oxazine (1235527-97-5)

Conditions	Yield
With montmorillonite K-10 at 30℃; for 0.166667h; Sonication;	98%
With Montmorillonite K-10 at 125℃; for 1.3h;	96%
With sulfur; cobalt(II) nitrate In neat (no solvent) at 90℃; for 0.05h; Reagent/catalyst; Solvent; Temperature; Time; Microwave irradiation;	95%
With phosphotungstic acid at 125℃; for 2h; chemoselective reaction;	90%
With sulfur In neat (no solvent) at 100℃; for 6h; Reagent/catalyst;	88%

pyridine-3-carbonitrile (100-54-9) + ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylate (4815-37-6) → 6-methyl-5-phenyl-2-(pyridin-3-yl)thieno[2,3-d]pyrimidin-4(3H)-one (724746-10-5)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 0℃; for 10h; Heating;	98%

pyridine-3-carbonitrile (100-54-9) + mesitylmagnesium bromide lithium chloride → 4-mesitylnicotinonitrile (1428419-76-4)

Conditions	Yield
Stage #1: pyridine-3-carbonitrile With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: mesitylmagnesium bromide lithium chloride In tetrahydrofuran at -30℃; for 2h; Inert atmosphere; Stage #3: With chloranil In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; regioselective reaction;	98%

pyridine-3-carbonitrile (100-54-9) + ethanol (64-17-5) → ethyl (3-pyridyl)imidate dihydrochloride (56624-12-5, 81659-46-3)

Conditions	Yield
With hydrogenchloride In dichloromethane at 0 - 20℃; for 1h;	97%
With acetyl chloride In chloroform for 25h; 0 deg C up to RT;	92%
With hydrogenchloride Kuehlung;
With hydrogenchloride In dichloromethane for 5h;

pyridine-3-carbonitrile (100-54-9) + Cysteamine (60-23-1) → 2-(pyridin-3-yl)-4,5-dihydrothiazole (3919-80-0)

Conditions	Yield
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.05h; chemoselective reaction;	97%
With tribromomelamine at 100℃; for 0.0833333h; Neat (no solvent);	94%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.1h; chemoselective reaction;	85%

pyridine-3-carbonitrile (100-54-9) + ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) → 2-(pyridin-3-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 0℃; for 10h; Heating;	97%
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	74%
With hydrogenchloride In 1,4-dioxane for 5h;	60%

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 626-55-1 3-Bromopyridine 
• 59-67-6 nicotinic acid 
• 70-55-3 toluene-4-sulfonamide 
• 98-10-2 benzenesulfonamide 
• 108-99-6 3-Methylpyridine 
• 98-92-0 nicotinamide 
• 110-86-1 pyridine 
• 460-19-5 ethanedinitrile 
• 500-22-1 3-pyridinecarboxaldehyde 
• 67-66-3 chloroform 
• 504-29-0 2-aminopyridine 
• 151-50-8 potassium cyanide 
• 51892-16-1 nicotinaldehyde oxime 

Downstream Products

• 35779-35-2 di-3-pyridylmethanone 
• 59576-33-9 2-(2-pyridinyl)-1-(3-pyridinyl)ethanone 
• 37128-50-0 (2-methyl-1H-indol-3-yl)-3-pyridinylmethanone 
• 37760-49-9 3-phenyl-5-(pyridin-3-yl)-1,2,4-oxadiazole 
• 5585-14-8 3,4-diphenyl-furazan 2-oxide 
• 63697-67-6 (E)-2-((2-(pyridin-3-yl)hydrazono)methyl)pyridine 
• 350-03-8 methyl-3-pyridylketone 
• 7247-93-0 3-cyano-1-methylpyridinium chloride 
• 18010-63-4 nicotinic acid-(1,1-dimethyl-2-phenyl-ethylamide) 
• 1701-72-0 1-(pyridin-3-yl)pentan-1-one 
• 1570-48-5 1-(pyridin-3-yl)propan-1-one 
• 51227-29-3 2-methyl-1-(pyridin-3-yl)propan-1-one 
• 1701-70-8 1-pyridin-3-yl-butan-1-one 
• 120445-71-8 Pyridin-3-aldehyd-semicarbazon 

Relevant academic research and scientific papers

Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: A biomimetic model for the H2O2-dependent activity of nitric oxide synthase

A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces N(δ)-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

Highly efficient synthesis of primary amides: Via aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex

The transformation of aldoximes to primary amides has been evaluated using pincer ruthenium complexes a-c, among which the ionic Ru catalyst a proved to be the most efficient in water under air atmosphere. A variety of (hetero)arene aldoximes proceeded smoothly to afford amides in high yields with good functional group compatibilities. Furthermore, a direct synthetic route of amides from aldehydes, hydroxylamine hydrochloride and sodium carbonate was also described with broad substrates including conjugated and aliphatic aldehydes. This protocol is operationally simple and proceeds with a low catalyst loading (0.5 mol%).

Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles

An economical and environmentally benign process for the preparation of nitriles by the dehydration of primary amides and aldoximes is catalyzed by rhenium(VII) oxo complexes such as perrhenic acid and trimethylsilylperrhenate (see scheme). The reaction proceeds at azeotropic reflux (with the removal of water) under essentially neutral conditions.

An indium mediated efficient chemoselective deoxygenation of N-oxides and nitrones

A simple and inexpensive procedure for the deoxygenation of N-oxides, such as N-arylnitrones, azoxybenzenes and N-heteroarene N-oxides with indium trichloride in acetonitrile at ambient pressure is described. The procedure gives high yields of deoxygenated products.

1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent

formula presented A mild and high-yielding cyanating reaction of amine, sulfur, and carbanion nucleophiles is reported here using 1-cyanoimidazole as an electrophilic cyanating agent.

Ternary VZrALON oxynitrides - Efficient catalysts for the ammoxidation of 3-picoline

Starting from previous binary VZrON (VAlON) oxynitrides with high (low) activity and low (high) selectivity, a new class of ternary VZrAlON catalysts has been developed for the ammoxidation of 3-picoline to 3-cyanopyridine (3-CP), which combine the benefi

Dispersion and 3-Picoline Ammonoxidation Investigation of V2O5/α-Al2O3 Catalysts

The effect of changing the precursor on the dispersion and 3-picoline ammonoxidation activity of various α-Al2O3 supported V2O5 catalysts has been investigated by the techniques of X-ray fluorescence, AES, SEM, EPR, XRD, oxygen chemisorption at 195 K and

Statistical experimental design-driven discovery of room-temperature conditions for palladium-catalyzed cyanation of aryl bromides

A combination of Pd2(dba)3·CHCl3 (0.5 mol %) and commercially available, air-stable phosphonium salt [(t-Bu) 3PH]BF4 (1.4 mol %) in a presence of Zn powder and Zn(CN)2 as the cyanide source comprises an extremely efficient catalyst system for the cyanation of a diverse array of aryl bromides, at room temperature. This result emerged from an experimental strategy that combines the advantages of parallel, automated experimentation with the design of experiments (DOE) for the effective definition of an optimal set of reaction conditions.

Perrhenic acid-catalyzed dehydration from primary amides, aldoximes, N-monoacylureas, and α-substituted ketoximes to nitrile compounds

The dehydration reaction of primary amides is one of the most fundamental methods for the synthesis of nitriles, and the development of environmentally benign catalytic reaction processes is needed. We surveyed a variety of metal catalysts and found that perrhenic acid was extremely effective for the dehydration of not only primary amides but also aldoximes. Typically, 1 mol % of perrhenic acid gave the corresponding nitriles from amides or aldoximes under azeotropic reflux conditions with the removal of water in toluene or mesitylene. In addition, perrhenic acid is an extremely efficient catalyst for the Beckmann fragmentation of α-substituted ketoximes to functionalized nitriles. This new catalytic system can be applied to the gram-scale synthesis of nitriles without further modifications.

Iodine/aqueous NH4OAc: An improved reaction system for direct oxidative conversion of aldehydes and alcohols into nitriles

A convenient method for direct oxidative conversion of aldehydes and alcohols into nitriles has been developed by using the inexpensive and environmentally friendly reagent I2/aqueous NH4OAc. The aqueous NH4OAc as a non-toxic cyanide source is more eco-friendly than aqueous ammonia, because gaseous ammonia evaporates easily from aqueous ammonia but not from aqueous NH4OAc.