4-Pyridinecarbonitrile

Cat.NO.:A118427 Purity:98%

Product Details of 4-Pyridinecarbonitrile

CAS No. :	100-48-1
Formula :	C₆H₄N₂
M.W :	104.11
SMILES Code :	N#CC1=CC=NC=C1
MDL No. :	MFCD00006417
InChI Key :	GPHQHTOMRSGBNZ-UHFFFAOYSA-N
Pubchem ID :	7506

Safety of 4-Pyridinecarbonitrile

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P362+P364-P501

Application In Synthesis of 4-Pyridinecarbonitrile

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 100-48-1 ]
Downstream synthetic route of [ 100-48-1 ]

[ 100-48-1 ] Synthesis Path-Upstream 1~8

1
[ 100-48-1 ]
[ 7677-24-9 ]
[ 29181-50-8 ]

References:

[1] Chemistry – A European Journal, 2017, vol. 23, # 59, p. 14733 – 14737.

2
[ 110-89-4 ]
[ 100-48-1 ]
[ 2767-90-0 ]

References:

[1] Tetrahedron Letters, 2004, vol. 45, # 12, p. 2667 – 2669.

3
[ 100-48-1 ]
[ 541-50-4 ]
[ 37398-49-5 ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; waterReflux	Step 1 : 2-Acetylisonicotinonitrile To a solution of isonicotinonitrile (52 g, 0.5 mol) in dichloromethane (1300 mL) and water (1 100 mL) were added ammonium persulfate ((NH₄)2S208) (170 g, 0.75 mol), silver nitrate (6.8 g, 0.04 mol) and aqueous sulfuric acid (40 mL, 98percent sulfuric acid in 400 mL). A solution of 3-oxo-butyric acid (1 10 g, 1.25 mol) in dichloromethane (100 mL) was added dropwise while keeping the mixture refluxing. The reaction mixture was refluxed for 2 h. The resulting mixture was basified to pH -8-9 using sodium carbonate powder. The mixture was filtered and the filtrate was extracted with dichloromethane (500 mL x 3). The combined organics were dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to afford 2-acetylisonicotinonitrile (52.0 g, 71.9percent).

References:

[1] Patent: WO2013/150416, 2013, A1, . Location in patent: Page/Page column 117.

4
[ 100-48-1 ]
[ 127-17-3 ]
[ 37398-49-5 ]

References:

[1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 – 2869.

5
[ 100-48-1 ]
[ 56-41-7 ]
[ 37398-49-5 ]

References:

[1] Organic Letters, 2016, vol. 18, # 15, p. 3738 – 3741.

6
[ 100-48-1 ]
[ 72-19-5 ]
[ 37398-49-5 ]

References:

[1] Organic Letters, 2016, vol. 18, # 15, p. 3738 – 3741.

7
[ 100-48-1 ]
[ 431-03-8 ]
[ 37398-49-5 ]

References:

[1] Journal of Chemical Research, Miniprint, 1982, # 10, p. 2801 – 2815.

[2] Journal of Chemical Research, Miniprint, 1982, # 10, p. 2801 – 2815.

8
[ 617-35-6 ]
[ 100-48-1 ]
[ 97316-50-2 ]
[ 97316-54-6 ]
[ 97316-52-4 ]
[ 97316-53-5 ]

References:

[1] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 – 695.

[2] Heterocycles, 1987, vol. 26, # 3, p. 731 – 744.

[3] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 – 695.

[4] Angewandte Chemie, 1985, vol. 97, # 8, p. 694 – 695.

[5] Heterocycles, 1987, vol. 26, # 3, p. 731 – 744.

[6] Heterocycles, 1987, vol. 26, # 3, p. 731 – 744.

[ 100-48-1 ] Synthesis Path-Downstream 1~17

1
[ 110-91-8 ]
[ 100-48-1 ]
[ 143798-67-8 ]

References: [1]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 975 – 977.

2
[ 100-48-1 ]
[ 26163-07-5 ]
6-dimethylamino-3-pyridyl 4-pyridyl ketone [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,1986,vol. 24,p. 897 – 899.

3
[ 100-48-1 ]
[ 127-17-3 ]
[ 37398-49-5 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 2866 – 2869.

4
[ 100-48-1 ]
[ 431-03-8 ]
[ 37398-49-5 ]
1,1′-(4-cyanopyridine-2,6-diyl)diethanone [ No CAS ]
2,5-diacetyl-4-cyanopyridine [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1982,p. 2801 – 2815.
[2]Journal of Chemical Research, Miniprint,1982,p. 2801 – 2815.

5
[ 123-75-1 ]
[ 100-48-1 ]
[ 2456-81-7 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 2667 – 2669.

6
[ 100-48-1 ]
[ 14062-29-4 ]
[ 556-61-6 ]
[ 74-88-4 ]
5-(3-chloro-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3<i>H</i>-pyrimidin-4-one [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 11714 – 11723.

7
[ 1455-20-5 ]
[ 100-48-1 ]
[ 1620-30-0 ]
C₁₃H₁₅NS [ No CAS ]

References: [1]Chemical Science,2013,vol. 4,p. 3118 – 3123.

8
[ 100-48-1 ]
[ 541-50-4 ]
[ 37398-49-5 ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With ammonium peroxydisulfate; sulfuric acid; silver nitrate; In dichloromethane; water;Reflux;	Step 1 : 2-Acetylisonicotinonitrile To a solution of isonicotinonitrile (52 g, 0.5 mol) in dichloromethane (1300 mL) and water (1 100 mL) were added ammonium persulfate ((NH4)2S208) (170 g, 0.75 mol), silver nitrate (6.8 g, 0.04 mol) and aqueous sulfuric acid (40 mL, 98% sulfuric acid in 400 mL). A solution of 3-oxo-butyric acid (1 10 g, 1.25 mol) in dichloromethane (100 mL) was added dropwise while keeping the mixture refluxing. The reaction mixture was refluxed for 2 h. The resulting mixture was basified to pH -8-9 using sodium carbonate powder. The mixture was filtered and the filtrate was extracted with dichloromethane (500 mL x 3). The combined organics were dried over sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to afford 2-acetylisonicotinonitrile (52.0 g, 71.9%).

References: [1]Patent: WO2013/150416,2013,A1 .Location in patent: Page/Page column 117.

9
[ 100-48-1 ]
[ 7579-20-6 ]
[ 1589081-35-5 ]

Yield	Reaction Conditions	Operation in experiment
6.02 g		Synthesis of 2-Pyridin-4-yl-pyrido[3,4-d]pyrimidin-4-ol [A001] A mixture of 4-Cyanopyridine (8.25 g, 79.2 mmol), sodium methoxide (891 mg, 16.5 mmol) and methanol (400 mL) was stirred at room temperature for 60 minutes. 3-Amino- isonicotinic acid (9.12g, 66.0 mmol) was added and the mixture heated to reflux for 3 days. After cooling to room temperature the solid precipitate was collected by filtration then dried in the vacuum oven to yield the title compound as an off-white solid (6.02 g): (IH, 300MHz, d6-dmso) 13.10 (IH, br s), 9.16 (IH, s), 8.80 (2H, dd), 8.70 (IH, d), 8.10 (2H, dd), 8.00 (IH, dd)
6.02 g		Synthesis of 2-Pyridin-4-yl-pyrido[3,4-d]pyrimidin-4-ol [A001] (0137) A mixture of 4-Cyanopyridine (8.25 g, 79.2 mmol), sodium methoxide (891 mg, 16.5 mmol) and methanol (400 mL) was stirred at room temperature for 60 minutes. 3-Amino-isonicotinic acid (9.12 g, 66.0 mmol) was added and the mixture heated to reflux for 3 days. After cooling to room temperature the solid precipitate was collected by filtration then dried in the vacuum oven to yield the title compound as an off-white solid (6.02 g): (1H, 300 MHz, d6-dmso) 13.10 (1H, br s), 9.16 (1H, s), 8.80 (2H, dd), 8.70 (1H, d), 8.10 (2H, dd), 8.00 (1H, dd)

References: [1]Patent: WO2014/52699,2014,A1 .Location in patent: Page/Page column 201.
[2]Patent: US2015/274720,2015,A1 .Location in patent: Paragraph 0137.

10
[ 100-48-1 ]
[ 175883-62-2 ]
3-(4-methoxyphenyl)isonicotinonitrile [ No CAS ]
3-(3-methyl-4-methoxyphenyl)isonicotinonitrile [ No CAS ]

References: [1]Chinese Journal of Chemistry,2014,vol. 32,p. 1294 – 1298.

11
[ 100-48-1 ]
[ 72-19-5 ]
[ 37398-49-5 ]

References: [1]Organic Letters,2016,vol. 18,p. 3738 – 3741.

12
[ 100-48-1 ]
[ 56-41-7 ]
2-acetyl-6-methylisonicotinonitrile [ No CAS ]
[ 37398-49-5 ]

References: [1]Organic Letters,2016,vol. 18,p. 3738 – 3741.

13
[ 100-48-1 ]
[ 98-80-6 ]
[ 3034-31-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium tert-butylate; copper(ll) bromide; In tert-butyl alcohol; at 20℃; for 37h;	General procedure: A 10 mL round-bottomed flask was charged with the appropriate nitrile 2 (0.50 mmol), arylboronic acid 1(0.60 mmol), CuBr2 (6 mg, 5mol%), t-BuOK (168 mg, 1.50 mmol), and t-BuOH (3.0 mL), and the mixture was stirred at r.t. until the reaction was complete (TLC). H2O (4.0 mL) was added, and the mixture was extracted with EtOAc (3 ×10 mL). The combined organic layers were washed twice with H2O,dried (Na2SO4), and concentrated to give a residue that was purified by column chromatography (silica gel, PE-EtOAc).

References: [1]Synthesis,2017,vol. 49,p. 1834 – 1838.

14
[ 100-48-1 ]
[ 7677-24-9 ]
[ 29181-50-8 ]

References: [1]Chemistry – A European Journal,2017,vol. 23,p. 14733 – 14737.

15
[ 100-48-1 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 3847-57-2 ]
2C₇H₄NO₄^(1-)*2C₆H₄N₂*Mn⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		Sodium salt of p-nitrobenzoic acid (0.189 g, 1.0 mmol) was dissolved in 15 ml distilled water in a round-bottom flask. An aqueous solution of MnCl2*4H2O (0.198 g, 1 mmol) was added to the above solution. The solution was then stirred at room temperature for about an hour. To the resulting colorless solution, 4-CNpy (0.208 g, 2 mmol) was added slowly and the mixture was stirred mechanically for about two hours (Scheme 2). The solution obtained was then filtered and left unperturbed for crystallization. Colorless crystals with irregular shape were obtained from the mixture after few weeks with a yield of 74% based on Mn. The large crystals were filtered off, washed with water and dried in air. Anal. Calcd. for C26H16Cl0MnN6O8: C, 49.50; H, 2.56;N, 13.32. Found: C, 49.30; H, 2.61; N, 13.20. IR (KBr pellet, cm-1): 3414 (m), 3092 (sh), 2235 (m), 1942 (m), 1612 (vs), 1547 (m), 1496(s), 1416 (vs), 1218 (s), 1115 (w), 1064 (m), 1005 (m), 831 (vs), 786 (m), 552 (m).

References: [1]Inorganica Chimica Acta,2019,vol. 487,p. 424 – 432.

16
[ 100-48-1 ]
[ 1428

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