59-26-7

Basic information

• Product Name: N,N-DIETHYLNICOTINAMIDE
• Synonyms: CORVOTONE;DYNACORYL;EUCORAN;LABOTEST-BB LT00134638;ANACARDONE;PYRIDINE-3-CARBOXYLIC ACID DIETHYLAMIDE;PYRICARDYL;N,N-DIETHYLNICOTINAMIDE
• CAS NO: 59-26-7
• Molecular Formula: C₁₀H₁₄N₂O
• Molecular Weight: 178.23
• EINECS: 200-418-5
• Product Categories: Nitrogen cyclic compounds;Heterocyclic Compounds;NIKETHYL
• Mol File: 59-26-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 23 °C(lit.)
• Boiling Point: 296-300 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0013mmHg at 25°C
• Refractive Index: n20/D 1.524(lit.)
• Storage Temp.: 2-8°C
• PKA: pKa 3.46(H2O,t =20) (Uncertain)
• Water Solubility: >=10 g/100 mL at 23 C
• Merck: 14,6543
• BRN: 5743
• CAS DataBase Reference: N,N-DIETHYLNICOTINAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYLNICOTINAMIDE(59-26-7)
• EPA Substance Registry System: N,N-DIETHYLNICOTINAMIDE(59-26-7)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-23/24/25
• Safety Statements: 26-45-36/37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: QS4375000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 59-26-7(Hazardous Substances Data)

Usage

Description

A further Corydalis alkaloid, coramine has been obtained from C. pseudoadunca M. Pop. It forms colourless needles from EtOH and is optically active with a specific rotation of [α]D - 391 ° (c 0.2, MeOH). Both the hydrochloride, m.p. 216-9°C and the hydrobromide, m.p. 223-6°C have been described.

Chemical Properties

clear colorless to yellow liquid

Uses

N,N-Diethylnicotinamide (DENC) is commonly used as a ligand to prepare tetranuclear copper complexes.

General Description

Clear light yellow viscous liquid or crystalline solid. Slightly bitter taste followed by a faint sensation of the warmth.

Air & Water Reactions

Water soluble.

Reactivity Profile

N,N-DIETHYLNICOTINAMIDE is incompatible with sodium carbonate solutions which cause precipitation. .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N,N-DIETHYLNICOTINAMIDE emits toxic fumes.

Fire Hazard

N,N-DIETHYLNICOTINAMIDE is combustible.

Safety Profile

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.

References

Yunusov, Akramov, Yunusov, Dokl. Akad. Nauk. USSR, 162,607 (1965) Yunusov, Akramov, Yunusov, Khim. Prir. Soedin., 2, 340 (1966) Ibragimova, Yunusov, Yunusov, ibid, 6,438 (1970) Yunusov, et al., ibid, 7, 380 (1971)

InChI:InChI=1/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3

Synthetic route

3-Bromopyridine (626-55-1) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 105℃; under 3000.3 Torr; for 12h;	92%
With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20 - 60℃; under 2068.65 Torr; for 24h; Inert atmosphere; Autoclave; chemoselective reaction;	92%
With palladium diacetate; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Sealed tube;	75%

nicotinic acid (59-67-6) + N-formyldiethylamine (617-84-5) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In 1,4-dioxane at 120℃; for 33h;	92%

3-(N,N-diethylcarbamoyl)pyridine 1-oxide (20165-96-2) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 2.5h; Inert atmosphere; Irradiation; chemoselective reaction;	92%

nicotinic acid (59-67-6) + hexaethylphosphoric triamide (2283-11-6) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
at 210℃; for 1h;	88%

methyl 3-pyridinecarboxylate (93-60-7) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
Stage #1: diethylamine With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.833333h; Stage #2: methyl 3-pyridinecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h;	84%
potassium tert-butylate at 285℃; under 22502.3 Torr; for 0.0116667h; autoclave; Industry scale; Microwave irradiation;

3-Bromopyridine (626-55-1) + chloroform (67-66-3) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With cesiumhydroxide monohydrate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 80℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;	79%

nicotinic acid (59-67-6) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
Stage #1: nicotinic acid With niobium pentachloride In 1,4-dioxane Stage #2: diethylamine In 1,4-dioxane at 45 - 50℃; for 12h;	73%
With phosphorus pentoxide
With phosphorus pentoxide; benzene
With trichlorophosphate
With N,N'-ethylenethiourea; bis(trichloromethyl) carbonate at 70℃; for 1h; Temperature; Reagent/catalyst; Green chemistry;

nicotinic acid (59-67-6) + diethyl amine hydrochloride (660-68-4) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With triethylamine at 20℃; for 0.0166667h;	72%
With silica gel; triethylamine; p-toluenesulfonyl chloride at 20℃; for 0.0166667h;	70%
With phosphorus pentachloride

carbon monoxide (201230-82-2) + 3-pyridylboronic acid (1692-25-7) + triethylamine (121-44-8) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With copper(l) iodide; oxygen; palladium dichloride In acetonitrile at 100℃; under 1520.1 Torr; for 12h; Autoclave; High pressure;	62%

N,N-dimethylnicotinamide (6972-69-6) + lithium diethylamide (816-43-3) → N,N-Dimethyl-4-(pyridine-3-carbonyl)-nicotinamide (77924-13-1) + N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
In diethyl ether for 5h; Ambient temperature;	A 6% B 60%

N,N-dimethylnicotinamide (6972-69-6) → N,N-Dimethyl-4-(pyridine-3-carbonyl)-nicotinamide (77924-13-1) + N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With lithium diethylamide In diethyl ether for 5h; Ambient temperature;	A 6% B 60%

N,N-dimethylnicotinamide (6972-69-6) + lithium diethylamide (816-43-3) → N,N-Dimethyl-4-(pyridine-3-carbonyl)-nicotinamide (77924-13-1) + N,N-diethylnicotinamide (59-26-7) + lithiated products

Conditions	Yield
In ethanol for 5h; Product distribution; Ambient temperature;	A 6% B 60% C n/a

3-pyridinecarboxylic acid ethyl ester (614-18-6) + dimethyl amine (124-40-3) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
sodium methylate In ethylene glycol at 85℃; for 25h; Conversion of starting material;	37%

3-pyridinecarboxylic acid ethyl ester (614-18-6) + hexaethylphosphoric triamide (2283-11-6) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
at 210 - 220℃; for 2h;	34.8%

nicotinic acid (59-67-6) + N,N,N',N'-tetraethylurea (1187-03-7) → N,N-diethylnicotinamide (59-26-7)

nicotinic acid (59-67-6) + N,N-diethylbenzenesulfonamide (1709-50-8) → N,N-diethylnicotinamide (59-26-7)

nicotinic acid (59-67-6) + N,N-diethyl-4-methylbenzenesulfonamide (649-15-0) → N,N-diethylnicotinamide (59-26-7)

3-pyridinecarbonyl chloride (10400-19-8) + diethyl amine hydrochloride (660-68-4) → N,N-diethylnicotinamide (59-26-7)

Pyridine-2,3-dicarboxylic anhydride (699-98-9) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
Erhitzen des Reaktionsprodukts auf 180grad;

3-Bromopyridine (626-55-1) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethyl-α-oxo-3-pyridineacetamide (84039-67-8) + N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
PdCl2(PMePh2)2 at 100℃; under 7600 Torr; for 63h; Yield given. Yields of byproduct given;

3-pyridinecarbonyl chloride (10400-19-8) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With pyridine In toluene at 60 - 90℃; for 4h;
With triethylamine In dichloromethane at 20℃; for 0.5h;

4-chloro-N,N-diethyl-3-pyridinecarboxamide (55675-97-3) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With hydrogen; palladium

pyridine-3-carbonyl chloride hydrochloride (20260-53-1) + diethylamine (109-89-7) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
In dichloromethane

N,N-diethylbenzenesulfonamide (1709-50-8) + nicotinic acid benzenesulfonate → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
at 200℃;

3-iodopyridine (1120-90-7) + carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N,N-diethyl-α-oxo-3-pyridineacetamide (84039-67-8) + N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With potassium phosphate; chloromethyl(1,5-cyclooctadiene)palladium(II) In 1,4-dioxane at 100℃; under 7600 Torr; for 15h;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Schlenk technique;

propylamine (107-10-8) + α-(3-pyridyl)-α-(4-morpholino)acetonitrile (36740-09-7) → [1-Morpholin-4-yl-1-pyridin-3-yl-meth-(Z)-ylidene]-propyl-amine + N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With nickel(IV) oxide In tetrahydrofuran at 20℃; for 16h;	A 97 % Chromat. B n/a

Diethyl-carbamic acid 3-diethylcarbamoyl-pyridin-4-yl ester (98976-84-2) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaOMe; 2.) POCl3 / 1.) MeOH 2: H2 / Pd View Scheme

nicotinic acid (59-67-6) + phenyl-β-pyridyl ketone → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, pyridine / toluene / 1 h / 90 °C 2: pyridine / toluene / 4 h / 60 - 90 °C View Scheme

nicotinic acid (59-67-6) → N,N-diethylnicotinamide (59-26-7)

Conditions	Yield
With trifluoroacetic acid In water; acetonitrile
Multi-step reaction with 2 steps 1: thionyl chloride / toluene; N,N-dimethyl-formamide / 20 °C 2: triethylamine / dichloromethane / 0.5 h / 20 °C View Scheme

N,N-diethylnicotinamide (59-26-7) → 3-pyridinecarboxaldehyde (500-22-1)

Conditions	Yield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h;	99%
With diethyl ether; diisobutylaluminium hydride

N,N-diethylnicotinamide (59-26-7) → N,N-diethyl-3-piperidinecarboxamide hydrochloride

Conditions	Yield
With 1,1,2-trichloroethane; palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 46h;	99%

N,N-diethylnicotinamide (59-26-7) → N,N-diethyl-α,α-dichloro-3-pyridylmethylamine (721451-34-9)

Conditions	Yield
With oxalyl dichloride In tert-butyl methyl ether at 20℃; for 5h; Heating / reflux;	95%
With oxalyl dichloride In tert-butyl methyl ether at 20℃; for 5h; Inert atmosphere; Reflux;	95%

C10H10FN3O + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 4-((S*)-5-fluoro-1,3-dimethyl-2-oxoindolin-3-yl)-3-(diethylcarbamoyl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C10H10FN3O With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	95%

N,N-diethylnicotinamide (59-26-7) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1,3-phenylenebis(methylene)[3-(N,N-diethyl)carbamoylpyridinium bromide]

Conditions	Yield
In acetonitrile for 18h; Heating;	94%

N,N-diethylnicotinamide (59-26-7) + 2-(1-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C21H24Cl4N2O3

Conditions	Yield
Stage #1: 2-(1-(4-methoxyphenyl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With (3,5-bis(trifluoromethyl)phenyl)lithium In tetrahydrofuran at -78℃; Stage #2: N,N-diethylnicotinamide; 2,2,2-Trichloroethyl chloroformate In tetrahydrofuran at -40℃; diastereoselective reaction;	94%

N,N-diethylnicotinamide (59-26-7) → 5,5'-di-(N,N-diethylcarbamido)-2,2'-dipyridyl

Conditions	Yield
With nickel at 180 - 190℃; for 10h;	93.2%

N,N-diethylnicotinamide (59-26-7) + 2-diazo-N-methyl-N-phenylpropanamide + Allyl chloroformate (2937-50-0) → (R*)-allyl 3-(diethylcarbamoyl)-4-((S*)-1,3-dimethyl-2-oxoindolin-3-yl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: 2-diazo-N-methyl-N-phenylpropanamide With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	93%

C10H10BrN3O + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 4-((S*)-5-bromo-1,3-dimethyl-2-oxoindolin-3-yl)-3-(diethylcarbamoyl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C10H10BrN3O With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	93%

copper(II) nitrate trihydrate + sodium coumarilate + N,N-diethylnicotinamide (59-26-7) → [Cu(II)(coumarilate)2(N,N'-diethylnicotinamide)2(H2O)2]

Conditions	Yield
Stage #1: sodium coumarilate; N,N-diethylnicotinamide In ethanol; water at 20℃; for 0.5h; Stage #2: copper(II) nitrate trihydrate In ethanol at 55℃; for 3h; Stage #3: In ethanol at 20℃; for 840h;	92%

C10H10ClN3O + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 4-((S*)-5-chloro-1,3-dimethyl-2-oxoindolin-3-yl)-3-(diethylcarbamoyl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C10H10ClN3O With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	91%

Diethyl 2-bromomalonate (685-87-0) + N,N-diethylnicotinamide (59-26-7) → C17H24N2O5

Conditions	Yield
at 20℃; for 360h;	90.4%

1,1-bis(trimethylsiloxy)-2-methylprop-1-ene (31469-25-7) + N,N-diethylnicotinamide (59-26-7) + methyl chloroformate (79-22-1) → methyl 4-(1-carboxy-1-methylethyl)-3-diethylcarbamoyl-4H-pyridine-1-carboxylate

Conditions	Yield
In dichloromethane at 20℃; for 2h;	90%

cadmium(II) p-chlorobenzoate hydrate + N,N-diethylnicotinamide (59-26-7) → Cd(p-chlorobenzoate)2(diethylnicotinamide)2(H2O)2*2H2O

Conditions	Yield
In water soln. of diethylnicotinamide in H2O added dropwise with stirring to soln. of p-chlorobenzoate in hot H2O; soln. heated to 50°C and stirred for 4 h; cooled to room temp.; allowed to stay 10-12 ds for crystn.; filtered; washed (cold water, acetone); dried (vac.); elem. anal.;	90%

C11H13N3O + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 3-(diethylcarbamoyl)-4-((S*)-1,3,5-trimethyl-2-oxoindolin-3-yl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C11H13N3O With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	90%

2-diazo-N-methyl-N-phenylacetamide (38118-70-6) + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 3-(diethylcarbamoyl)-4-((S*)-1-methyl-2-oxoindolin-3-yl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: 2-diazo-N-methyl-N-phenylacetamide With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	90%

bromoacetic acid (-)-8-phenylmenthol ester (80595-59-1) + N,N-diethylnicotinamide (59-26-7) → 3-(N,N-diethylaminocarbonyl)-1-(l-8-phenylmenthyloxycarbonylmethyl)pyridinium bromide

Conditions	Yield
at 90℃;	89%

N,N-diethylnicotinamide (59-26-7) → α-deuterio-3-pyridinecarboxaldehyde (42007-11-4)

Conditions	Yield
With zirconocene dichloride; diisobutylaluminium deuteride In tetrahydrofuran at 0 - 23℃;	89%

methylbis(trimethylsilyloxy)vinylsilane (5356-85-4) + N,N-diethylnicotinamide (59-26-7) → N,N-diethyl-6-(2-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)ethyl)nicotinamide

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); C85H88N2O2; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum at 135℃; for 18h; Inert atmosphere; Glovebox; regioselective reaction;	89%

C11H13N3O2 + N,N-diethylnicotinamide (59-26-7) + Allyl chloroformate (2937-50-0) → (R*)-allyl 3-(diethylcarbamoyl)-4-((S*)-5-methoxy-1,3-dimethyl-2-oxoindolin-3-yl)pyridine-1(4H)-carboxylate

Conditions	Yield
Stage #1: N,N-diethylnicotinamide; Allyl chloroformate In tetrahydrofuran at -20℃; for 0.166667h; Molecular sieve; Stage #2: C11H13N3O2 With bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at -20℃; for 13h; diastereoselective reaction;	88%

o-TolMgBr·LiCl + N,N-diethylnicotinamide (59-26-7) → N,N-diethyl-4-(o-tolyl)nicotinamide (1428419-68-4)

Conditions	Yield
Stage #1: N,N-diethylnicotinamide With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: o-TolMgBr·LiCl In tetrahydrofuran at -30℃; for 2h; Inert atmosphere; Stage #3: With chloranil In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; regioselective reaction;	87%

(S)-4,4,5,5-tetramethyl-2-(1-phenylpropyl)-1,3,2-dioxaborolane (1189120-03-3) + N,N-diethylnicotinamide (59-26-7) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → C22H27Cl3N2O3

Conditions	Yield
Stage #1: (S)-4,4,5,5-tetramethyl-2-(1-phenylpropyl)-1,3,2-dioxaborolane With (3,5-bis(trifluoromethyl)phenyl)lithium In tetrahydrofuran at -78℃; Stage #2: N,N-diethylnicotinamide; 2,2,2-Trichloroethyl chloroformate In tetrahydrofuran at -40℃; diastereoselective reaction;	87%

N,N-diethylnicotinamide (59-26-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C16H27BN2O3

Conditions	Yield
With ZrIII6(μ3-O)4(μ3-ONa)4H6Na6(1,3,5-benzenetricarboxylate)2 at 90℃; for 18h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique;	87%
With ammonium tetraphenylborate In [D3]acetonitrile at 90℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; regioselective reaction;	79%

zinc(II) nitrate hexahydrate + sodium coumarilate + N,N-diethylnicotinamide (59-26-7) → [Zn(II)(N,N'-diethylnicotinamide)2(H2O)4](coumarilate)2

Conditions	Yield
Stage #1: sodium coumarilate; N,N-diethylnicotinamide In ethanol; water at 20℃; for 0.5h; Stage #2: zinc(II) nitrate hexahydrate In ethanol at 55℃; for 3h; Stage #3: In ethanol at 20℃; for 840h;	87%

N,N-diethylnicotinamide (59-26-7) → 3-(N,N-diethylaminomethyl)pyridine (2055-14-3)

Conditions	Yield
With n-butyllithium; borane-THF; diisopropylamine at 65℃; for 2h;	86%
With phenylsilane; potassium hydroxide In neat (no solvent) at 20℃; for 16h;	80%
With diethylzinc; lithium chloride In tetrahydrofuran; hexane at 20℃; for 24h; Catalytic behavior; Inert atmosphere; chemoselective reaction;	72%

zinc(II) p-chlorobenzoate hydrate + N,N-diethylnicotinamide (59-26-7) → Zn(p-chlorobenzoate)2(diethylnicotinamide)2(H2O)2 (1039102-80-1)

Conditions	Yield
In water soln. of diethylnicotinamide in H2O added dropwise with stirring to soln. of p-chlorobenzoate in hot H2O; soln. heated to 50°C and stirred for 4 h; cooled to room temp.; allowed to stay 10-12 ds for crystn.; filtered; washed (cold water, acetone); dried (vac.); elem. anal.;	86%

Upstream product

• 6972-69-6 N,N-dimethylnicotinamide 
• 816-43-3 lithium diethylamide 
• 1120-90-7 3-iodopyridine 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 80105-85-7 (C₁₀H₁₄N₂O)4Cu₄Cl₄O₂ 
• 41127-86-0 (C₉H₉N₂S₂)2Ni 
• 66514-12-3 bis(S-methyl-N-isopropylidendithiocarbazate)nickel(II) 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 1692-25-7 3-pyridylboronic acid 
• 121-44-8 triethylamine 
• 20165-96-2 3-(N,N-diethylcarbamoyl)pyridine 1-oxide 
• 59-67-6 nicotinic acid 

Downstream Products

• 500-22-1 3-pyridinecarboxaldehyde 
• 100-55-0 3-hydroxymethylpyridin 
• 2055-14-3 3-(N,N-diethylaminomethyl)pyridine 
• 177664-01-6 [Cu(H₂O)2(C₁₄H₉F₃NO₂)2(NC₅H₄CON(C₂H₅)2)2] 
• 1334721-96-8 [Cu(4-fluorosalicylate)2(N,N-diethylnicotinamide)2(H₂O)2] 
• 37704-97-5 1-(benzoylamino)-3-[(diethylamino)carbonyl]pyridinium ylide 
• 904701-57-1 3-[(diethylamino)carbonyl]-1-[(4-methoxyphenylsulfonyl)imino]pyridinium ylide 
• 904701-54-8 1-(4-aminobenzoylimino)-3-diethylcarbamoyl-pyridinium ylide 
• 904701-52-6 1-[(4-chlorobenzoyl)imino]-3-[(diethylamino)carbonyl]pyridinium ylide 

Relevant articles and documents

Pd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C-N Bond Activation

An efficient synthesis of tertiary amides from aryl boronic acids and inert tertiary amines through the oxidative carbonylation via C(sp3)-N bond activation is presented. This protocol significantly restricts the homocoupling biarylketone product. It involves the use of a homogeneous PdCl2/CuI catalyst and a heterogeneous Pd/C based catalyst, which promotes C(sp3)-N bond activation of tertiary amines with aryl boronic acids. This process represents a ligand-free, base-free, and recyclable catalyst along with an ideal oxidant like molecular oxygen.

A predictive model for additions to: N -alkyl pyridiniums

Disclosed in this communication is a thorough study on the dearomative addition of organomagnesium nucleophiles to N-alkyl pyridinium electrophiles. The regiochemical outcomes have observable and predictable trends associated with the substituent patterns on the pyridinium electrophile. Often, the substituent effects can be either additive, giving high selectivities, or ablative, giving competing outcomes. Additionally, the nature of the organometallic nucleophilic component was also investigated for its role in the regioselective outcome. The effects of either reactive component are important to both the overall reactivity and site of nucleophilic addition. The utility of these observed trends is demonstrated in a concise, dearomative synthesis of a tricyclic compound shown to have insecticidal activity. This journal is

Palladium nanoparticles on a pyridinium supported ionic liquid phase: a recyclable and low-leaching palladium catalyst for aminocarbonylation reactions

A new SILP (Supported Ionic Liquid Phase) palladium catalyst was prepared and characterized by 13C and 29Si CP MAS NMR, DTG, FTIR and TEM. The presence of the grafted pyridinium cations on the surface of the support was found to result in the formation of highly dispersed Pd nanoparticles with their diameter in the range of 1-2 nm. The catalyst was proved to be active not only in the aminocarbonylation of some model compounds but also in the synthesis of active pharmaceutical ingredients. Catalyst recycling and palladium leaching studies were carried out for the first time in aminocarbonylations leading to CX-546(1-(1,4-benzodioxan-6-ylcarbonyl)piperidine), Moclobemide, Nikethamide and a precursor of Finasteride. The latter reaction proves that not only aryl iodides but also an iodoalkene can be converted into the products with the help of the heterogeneous catalyst. The results show that the conditions should be always fine-tuned in the reactions of different substrates to achieve optimal results. Palladium loss was also observed to depend considerably on the nature of the reaction partners. This journal is