28141-13-1

Basic information

• Product Name: 1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• Synonyms: 1-ethyl-1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-py;1-ethyl-1,2-dihydro-6-hydroxy-4-methyl-2-oxo-3-pyridinecarbonitril;3-PYRIDINECARBONITRILE,1-ETHYL-1,2-HYDRO-6-HYDROXY;3-CYANO-N-ETHYL-6-HYDROXY-4-METHYLPYRIDONE;3-CYANO-4-METHYL-6-HYDROXY-N-ETHYL-2-PYRIDONE;3-CYANO-4-METHYL-6-HYDROXY-N-ETHYL PYRIDONE;1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile;1-ETHYL-1,2-DIHYDRO-6-HYDROXY-4-METHYL-2-OXO-3-PYRIDINECARBONITRILE
• CAS NO: 28141-13-1
• Molecular Formula: C₉H₁₀N₂O₂
• Molecular Weight: 178.19
• EINECS: 248-865-5
• Product Categories: Intermediates of Dyes and Pigments;Pyridines;E-F;Stains and Dyes;Stains&Dyes, A to
• Mol File: 28141-13-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 244-247 °C(lit.)
• Boiling Point: 316.82 °C at 760 mmHg
• Flash Point: 145.408 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 7.99E-05mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Dimethylformamide
• PKA: 3.79±0.58(Predicted)
• CAS DataBase Reference: 1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile(28141-13-1)
• EPA Substance Registry System: 1-Ethyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile(28141-13-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 28141-13-1(Hazardous Substances Data)

Usage

Uses

2,3,4,5-Tetrabromoaniline is an intermediate in the synthesis of PBB 180 (P215190), a brominated biphenyls that can be used as a flame retardant and often incorporated into consumer products including appliances, electronics and plastics.

InChI:InChI=1/C9H10N2O2/c1-3-11-8(12)4-6(2)7(5-10)9(11)13/h4,13H,3H2,1-2H3

Synthetic route

ethyl acetoacetate (141-97-9) + ethylamine (75-04-7) + methyl 2-cyanoacetate (105-34-0) → 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1)

Conditions	Yield
With silica gel for 0.0333333h; microwave irradiation;	94%

ethylamine (75-04-7) + acetoacetic acid methyl ester (105-45-3) + ethyl 2-cyanoacetate (105-56-6) → 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1)

Conditions	Yield
With silica gel for 0.0333333h; microwave irradiation;	94%

ethyl acetoacetate (141-97-9) + ethylamine (75-04-7) + ethyl 2-cyanoacetate (105-56-6) → 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1)

Conditions	Yield
With silica gel for 0.0333333h; microwave irradiation;	93%

ethylamine (75-04-7) + acetoacetic acid methyl ester (105-45-3) + methyl 2-cyanoacetate (105-34-0) → 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1)

Conditions	Yield
With silica gel for 0.0333333h; microwave irradiation;	93%
In water

4,4'-diamino-2,2'-biphenyldisulfonic acid (117-61-3) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C30H26N8O10S2

Conditions	Yield
Stage #1: 4,4'-diamino-2,2'-biphenyldisulfonic acid With sodium hydroxide; sodium nitrite In water for 0.5h; pH=7 - 8; Cooling with ice; Stage #2: With hydrogenchloride In water for 2h; Stage #3: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone Further stages;	100%

4-(Aminophenyl)-sulfonylessigsaeure (83048-63-9) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C17H16N4O6S

Conditions	Yield
Stage #1: 4-(Aminophenyl)-sulfonylessigsaeure With hydrogenchloride; sodium nitrite In water at -5 - 0℃; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium hydroxide In water at -5 - 10℃; pH=5.5 - 6;	97.67%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + 4-aminobenzene sulfonic acid (121-57-3) → C15H14N4O5S

Conditions	Yield
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide In water pH=7 - 8; Cooling with ice; Stage #2: With hydrogenchloride; sodium nitrite In water for 2.5h; Cooling with ice; Stage #3: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In water for 2h; pH=8 - 9; Cooling with ice;	92%
Stage #1: 4-aminobenzene sulfonic acid With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 3h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium hydroxide In water at 10℃; pH=5 - 8;	78%
Stage #1: 4-aminobenzene sulfonic acid With hydrogenchloride; sodium nitrite In water at 5 - 10℃; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium hydroxide In water at 10℃; pH=5 - 8;	60.4 g

2-Amino-4,5,6,7-tetrahydrobenzothiazole (2933-29-1) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-4-methyl-2-oxo-5-[4,5,6,7-tetrahydro-1,3-benzothiazol-2 yldiazenyl]-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
Stage #1: 2-Amino-4,5,6,7-tetrahydrobenzothiazole With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With acetic acid In water at 0 - 5℃; for 2h;	88%

C12H11BrN3O2(1+)*HO4S(1-) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C21H20BrN5O4

Conditions	Yield
With sodium hydroxide; 2,4,7,9-tetramethyl-5-decyne-4,7-diol In water at 10 - 15℃; for 1.5h; pH=2 - 12;	86%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + anthranilic acid (118-92-3) → C16H14N4O4

Conditions	Yield
Stage #1: anthranilic acid With sulfuric acid; acetic acid; sodium nitrite In water for 0.5h; Cooling with ice; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In ethanol; water at 0 - 5℃; for 3h;	86%

2-Amino-4-phenylthiazole (2010-06-2) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → (E)-1-ethyl-6-hydroxy-4-methyl-2-oxo-5-((4-phenylthiazol-2-yl)diazenyl)-1,2-dihydropyridine-3-carbonitrile (1449324-68-8)

Conditions	Yield
Stage #1: 2-Amino-4-phenylthiazole With nitrosylsulfuric acid; sodium nitrite at 0 - 5℃; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium acetate; sodium hydroxide In water at 0 - 5℃; pH=6 - 7;	85%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 6-chloro-1-ethyl-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
With trichlorophosphate at 80℃;	84%
With trichlorophosphate for 3h; Reflux;	64%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + 4-amino-benzoic acid (150-13-0) → C16H14N4O4

Conditions	Yield
Stage #1: 4-amino-benzoic acid With sulfuric acid; acetic acid; sodium nitrite In water for 0.5h; Cooling with ice; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In ethanol; water at 0 - 5℃; for 3h;	84%

2-amino-4-chloro-5-formyl-3-cyanothiophene (104366-23-6) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → (Z)-5-((5-amino-3-chloro-4-cyanothiophen-2-yl)methylene)-1-ethyl-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

Conditions	Yield
With acetic anhydride at 90℃; for 2h;	78%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + 4-methoxy-aniline (104-94-9) → 1-ethyl-6-hydroxy-5-((4-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile (104495-77-4)

Conditions	Yield
Stage #1: 4-methoxy-aniline With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With potassium hydroxide In water at -5 - 5℃; for 3.5h;	73%

6-methylbenzothiazol-2-ylamine (2536-91-6) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-4-methyl-5-[(E)-(6-methyl-1,3-benzothiazol-2-yl)diazenyl]-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
Stage #1: 6-methylbenzothiazol-2-ylamine With nitrosylsulfuric acid; acetic acid In propionic acid at 0 - 5℃; for 3h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium carbonate In propionic acid at 0 - 4℃; for 2h; pH=6 - 7;	73%

2-thiazolylamine (96-50-4) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-4-methyl-2-oxo-5-[1,3-thiazol-2-yldiazenyl]-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
Stage #1: 2-thiazolylamine With sulfuric acid; acetic acid; propionic acid; sodium nitrite at 0 - 5℃; for 2.33333h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With potassium hydroxide In water at 0 - 5℃; for 2h; pH=5 - 6;	70%

C20H28N4O4S2 + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C38H42N10O8S2

Conditions	Yield
Stage #1: C20H28N4O4S2 With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium hydroxide In water at 10℃; pH=8;	69%

6-methoxybenzothiazol-2-ylamine (1747-60-0) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-5-[(E)-(6-methoxy-1,3-benzothiazol-2-yl)diazenyl]-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
Stage #1: 6-methoxybenzothiazol-2-ylamine With nitrosylsulfuric acid; acetic acid In propionic acid at 0 - 5℃; for 3h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With sodium carbonate In propionic acid at 0 - 4℃; for 2h; pH=6 - 7;	69%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + 4-methoxy-2-nitroaniline (96-96-8) → (Z)-1-ethyl-5-(2-(4-methoxy-2-nitrophenyl)hydrazono)-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile (1399166-04-1)

Conditions	Yield
Stage #1: 4-methoxy-2-nitroaniline With hydrogenchloride; sodium nitrite In water at -5℃; for 0.5h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In methanol; water at 0 - 5℃; for 3h;	68%

m-Anisidine (536-90-3) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-5-((3-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile (881069-36-9)

Conditions	Yield
Stage #1: m-Anisidine With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With potassium hydroxide In water at -5 - 5℃; for 3.5h;	67%

2-amino-5-nitro-1,3-thiazole (121-66-4) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-4-methyl-5-[-(5-nitro-1,3-thiazol-2-yl)diazenyl]-2-oxo-1,2-dihydropyridine-3-carbonitrile

Conditions	Yield
Stage #1: 2-amino-5-nitro-1,3-thiazole With phosphoric acid at 0 - 5℃; for 0.166667h; Stage #2: With sulfuric acid; sodium nitrite for 2.25h; Stage #3: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In acetic acid at 0 - 5℃; for 1.16667h;	60%

2-methoxy-phenylamine (90-04-0) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-5-((2-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile (881070-11-7)

Conditions	Yield
Stage #1: 2-methoxy-phenylamine With hydrogenchloride; sodium nitrite In water at -5℃; for 1h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone With potassium hydroxide In water at -5 - 5℃; for 3.5h;	58%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + N,N'-diphenylformamidine (864131-95-3) + 1,1'-[4,5,6-tris(n-dodecan-1-yloxy)-1,3-phenylenebis(methylene)]bis(4-methylpyridinium) dibromide → (5Z,5'Z)-5,5'-{[4,5,6-tris(dodecyloxy)-1,3-phenylene]bis[methylenepyridin-1-yl-4-ylidene(1Z)ethane-2,1-diylidene]}bis(1-ethyl-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile)

Conditions	Yield
Stage #1: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone; N,N'-diphenylformamidine In acetic anhydride at 20 - 90℃; for 0.75h; Stage #2: 1,1'-[4,5,6-tris(n-dodecan-1-yloxy)-1,3-phenylenebis(methylene)]bis(4-methylpyridinium) dibromide With potassium acetate In acetic anhydride at 105℃; for 20h; Further stages.;	42%

4-(trifluoromethanesulfonyl)aniline (473-27-8) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-6-hydroxy-4-methyl-2-oxo-5-(4-trifluoromethanesulfonyl-phenylazo)-1,2-dihydro-pyridine-3-carbonitrile

Conditions	Yield
Stage #1: 4-(trifluoromethanesulfonyl)aniline With sulfuric acid; sodium nitrite In N,N-dimethyl-formamide at 0℃; for 3h; Stage #2: 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone In N,N-dimethyl-formamide at 20℃; Further stages.;	40%

3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) + 3-azido-3-ethyl-1,3-benzothiazolium-tetrafluoroborat → (2-Amino-3-ethylbenzothiazolium)-5-cyano-3-<2-(5-cyano-1-ethyl-1,2,3,6-tetrahydro-4-methyl-2,6-dioxopyridin-3-yliden)hydrazino>-1-ethyl-1,6-dihydro-4-methyl-6-oxopyridin-2-olat

Conditions	Yield
In N,N-dimethyl-formamide at 0℃; for 2h;	27%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → 1-ethyl-4-methyl-2,5,10-trioxo-1,2,5,10-tetrahydro-naphtho[2',3':4,5]furo[2,3-b]pyridine-3-carbonitrile (71684-03-2)

Conditions	Yield
With pyridine In ethanol Heating;

2,3-difluoro-4-ethoxybenzoic acid (124728-45-6) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C18H16F2N2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ISOPROPYLAMIDE

2,6-difluoro-4-heptynylbenzoic acid (749900-86-5) + 3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone (28141-13-1) → C23H22F2N2O3

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ISOPROPYLAMIDE for 16h;

Upstream product

• 75-04-7 ethylamine 
• 105-45-3 acetoacetic acid methyl ester 
• 105-34-0 methyl 2-cyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 141-97-9 ethyl acetoacetate 

Relevant articles and documents

An Efficient Method for the Synthesis of 3-Cyano-6-hydroxy-2(1H)- pyridinones under Microwave Irradiation and Solvent-free Conditions

Three component condensation of alkylacetoacetates, primary amines, and alkyl cyanoacetates catalyzed by solid supports under microwave irradiation gave N-alkyl 3-cyano-6-hydroxy-2(1H)-pyridinones with high yields. Upon carrying out the reaction under the same condition on acidic alumina, zeolite HY, silica gel, and montmorillonite K-10, the best yields were achieved by silica gel.

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