Category: nitriles-buliding-blocks

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 31643-49-9, name is 4-Nitrophthalonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31643-49-9

The synthesis of 2 was similar to 1, but 4-hydroxybenzaldehyde wasemployed instead of dimethoxy phenyl ethanol. The reaction mixturewas stirred under N2 at room temperature for 24 h. The other reagentswere 4-nitrophthalonitrile (1 g, 5.55 mmol) and anhydrous K2CO3 (2 g,13.88 mmol). Compound 2 was obtained as: White solid; m.p. 350 C;yield 67%; FTIR (KBr) (n cm-1): 3077 (Ar-CH), 2227 (C?N), 1601(C=C), 1263 (C-O-C); 1H NMR (400 MHz, DMSO-d6): delta 7.49 (d,1H, H2¡é), 7.56 (d, 1H, H6¡é), 7.70 (d,1H, H3¡é), 7.74 (d, 1H, H5¡é), 7.86 (d,1H, H5), 7.89 (s, 1H, H3), 8.15 (d, 1H, H6), 10.02 (s, 1H, Hald); 13C NMR(100 MHz, DMSO-d6, tamb): delta 109.3 (C1), 115.7 (C2), 116.2 (C4¡é), 117.3(CN), 116.2 (CN), 120.8 (C2¡é), 123.6 (C6¡é), 126.7 (C3¡é,5¡é), 132.0 (C3),136.8 (C5), 138.8 (C6), 155.1 (C4), 160.8 (C1¡é), 192.7 (Cald); ESI-SMHRm/z: 249.23 [M + H]+. Anal. calcd for C15H8N2O2: C, 72.57; H, 3.24; N,11.28; found: C, 72.4; H, 3.1; N, 11.2%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Medyouni; Hallouma; Mansour; Al-Quraishy; Hamdi; Journal of Chemical Research; vol. 41; 5; (2017); p. 291 – 295;,
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Application of 2469-99-0, These common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: First of all, a mixture of 3-oxoalkanonitrile (1 mmol) and hydrazine hydrate (55% aq) (2 mmol) was magnetically stirred in ethanol (5 ml) for 2h under room temperature condition. After completion of the reactions, which was followed by TLC EtOAc:n-hexane 3:1, 2-phthaldehydic acid (1 mmol), CH-acid (1 mmol), and 4-toluenesulfonic acid (0.3mmol) as catalyst were added. Then, the mixture magnetically stirred for 22 h under reflux condition. Reaction solvent was removed by vacuum and participate was washed with methanol. Finally, the residue was purified by recrystallization in mixture of DMSO/methanol (5:2).

The synthetic route of 2469-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alizadeh-Kouzehrash, Meysam; Rahmati, Abbas; Tetrahedron; vol. 76; 7; (2020);,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 102151-33-7, name is 3-Chloro-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 3-Chloro-4-methoxybenzonitrile

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of 3-chloro-4-methoxybenzonitrile (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++1)

The synthetic route of 102151-33-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P.V.K. Suresh; Scola, Paul Michael; (403 pag.)US9527885; (2016); B2;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 61150-58-1, name is 2-(2-Bromo-4-fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 61150-58-1

Add potassium hydroxide (8.39 g, 150 mmol) and tetrabutylamine bromide(0.3 g, catalytic) to a solution of 2-(2-bromo-4-fluorophenyl)acetonitrile (4 g, 18.69 mmol) and 1,3-dibromopropane (4.15 g, 20.5 mmol) in toluene (20 mL). Stir it at 100 0C temperature for 2 h. Dilute the mixture with water and extract with ethyl acetate. Wash the organic layer with 1 N HCl and aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the crude product.Distill to give l-(2-bromo-4-fluorophenyl)cyclobutanecarbonitrile (boiling point 110- 120 C/0.3 Torr.) (1.5 g, 31 %). MS (GC) m/z 253 [M]+.Add 6 mL of HCl saturated methanol to the above solid and stir overnight. Evaporate the solvent to dry. Add NaHCO3 (1 M, 30 mL) and ether (20 mL). Stir for 15 min. Separate the organic layer and extract the aqueous layer with ether. Combine the ether solution and remove the solvent. Dissolve the residue in methanol (10 mL) and KOH (1.5 g) and stir over the weekend. Remove methanol and add water (30 mL). Extract with ethyl acetate and then acidify the aqueous layer with HCl. Extract the acidic solution with ethyl acetate, dry over MgSO4, and remove the solvent to give the title compound (1.0 g, 24 %). MS (ES) m/z 271 [M-I]”.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
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Related Products of 38469-83-9, The chemical industry reduces the impact on the environment during synthesis 38469-83-9, name is 4-Methoxy-2-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 2-Amino-4-methoxybenzamide To a solution of 37.4 g (0.210 mol) of 4-cyano-3-nitroanisole in 500 mL of ethanol was added 221.6 g (0.982 mol) of tin(II) chloride dihydrate. The reaction mixture was stirred and heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was poured onto ice. Aqueous sodium bicarbonate was added slowly to the ice mixture until the solution reached pH 7-8. Additional water was added to the mixture, which was then extracted with methylene chloride (2*400 mL) and ethyl acetate (1*300 mL). The separated aqueous layers were filtered between each of the extractions. The off white residue collected on the filters was rinsed with methylene chloride and ethyl acetate several times. The combined organic phases were then dried over magnesium sulfate, filtered and evaporated in the rotary evaporator to obtain 28.5 g crude product (mp 154-155 C.). Elemental analysis for C8 H10 N2 O2: Calc’d: C, 57.82; H, 6.07; N, 16.86; Found: C, 57.95; H, 5.95; N, 16.78.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Methoxy-2-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; American Home Products Corporation; US5948775; (1999); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 10406-25-4

General procedure: In a stainless reactor bomb, the corresponding aliphatic amine (1.0mmol), 1c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred under indicated conditions. After removing MeOH under reduced pressure, the products were isolated by silicagel column chromatography.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 10406-25-4.

Reference:
Article; Toyooka, Genki; Tuji, Akiko; Fujita, Ken-Ichi; Synthesis; vol. 50; 23; (2018); p. 4617 – 4626;,
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Application of 439117-38-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 439117-38-1 as follows.

Step C. [2-(aminomethyl)-5-chlorophenyl]methanol To LAH (1 M/Et2O, 104.4 ml, 104.4 mmol) in anhydrous THF (300 ml) at0 C. was added methyl 5-chloro-2-cyanobenzoate (9.28 g, 0.512 mmol) maintaining the temperature below 20 C. After one half hour, quenched at 0 C. with water (3.97 ml), NaOH (1N, 11.9 ml, 11.9 mmol) and water (3.97 ml). A precipitate was filtered out and washed with THF. The filtrate was concentrated in vacuo and was used immediately in the next step. H NMR (CDCl3, 400 MHz): delta7.17-7.36 (m, 3 H); 4.60 (s, 2 H); 3.98 (s, 2 H);

According to the analysis of related databases, 439117-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Barrow, James C.; Coburn, Craig; Selnick, Harold G.; Ngo, Phung L.; US2002/193398; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 103146-25-4, Safety of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Experiment 4: The general procedure of Experiment 2 was applied. To the 4-[4-(dimethylamino)- l-(4′-fluorophenyl)-l-hydroxybutyl]-3-(hydroxymethyl)-benzonitrile free base solution in 1-propanol was added 0.05 V of water. No toluene or acetic acid was present in the system. An exemplary batch gave molar yield: 29.3%; enantiomeric purity: 99.3% S.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
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Application of 3759-28-2,Some common heterocyclic compound, 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, molecular formula is C9H6N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Cyanomethyl)benzonitrile, its application will become more common.

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
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Application of 2920-38-9,Some common heterocyclic compound, 2920-38-9, name is [1,1′-Biphenyl]-4-carbonitrile, molecular formula is C13H9N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 4-cyanobiphenyl 2a (1.0 mmol, 179.2 mg) in THF (8.0 mL) were added aq. NH3 (28%, 10.0 mL) and KI (3.0 mmol, 498.0 mg) at 0 C. Aq. H2O2 (30%, 10.0 mL) was added dropwise to the mixture. The obtained mixture was stirred for 2 h at room temperature. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to give 4-biphenylcarboxamide 4a (183.4 mg, 93%). 4.5.1. 4-Biphenylcarboxamide (4a) Yield: 183.4 mg (93%); white solid; Mp 223 C: IR (neat) 3404, 3170, 1644, 1614, 1407 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 6.51-5.54 (m, 2H), 6.61 (dd, 2H, J = 6.8, 7.7 Hz), 6.84-6.89 (m, 4H), 7.10 (d, 2H, J = 6.8 Hz), 7.17 (s, 1H); 13C{1H}NMR (100 MHz, DMSO-d6): delta = 126.5, 126.9, 128.0, 128.2, 129.0, 133.1, 139.2, 142.8, 167.6; HRMS (ESI) Calcd for C13H12ON [M+H]+ = 198.0913, Found = 198.0915.

The synthetic route of 2920-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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