Category: 25978-68-1

Reference of 25978-68-1, These common heterocyclic compound, 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate, 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.

Lithium borohydride (33 mg, 1.54 mmol) was added into a solution of methyl 4-cyano-3- methylbenzoate (245 mg, 1.40 mmol) in THF (3 ml.) and the resulting mixture was stirred at RT for 4 hours. The reaction mixture was diluted with water (10 ml.) and extracted with EtOAc (4×20 ml_). The combined organic fractions were dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (silica, petrol ether/EtOAc) to give the title compound as a colorless gum (195 mg, 95%). 1H NMR (CDCI3, 400 MHz) delta 7.58 (1 H, d, J=7.9 Hz), 7.33 (1 H, s), 7.26 (1 H, m), 4.74 (2H, s), 2.55 (3H, s), 1.95 (1 H, s). LC/MS (Method A): 144 (M+H)+. HPLC (Method F) Rt 3.95 min (Purity: 95.3%).

The synthetic route of 25978-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 25978-68-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-cyano-3-methyl-benzoic acid methyl es­terfrom Example E2h.l (1.6g, 9.3mmol) in methanol (50ml) to 0C was treated with cobalt(II) chloride hexahydrate (5.1g, 18.6mmol). The mixture was stirred for 15min at room temperature then sodium borohydride (3.5g, 93mmol) was added portionwise. The reaction mixture was stirred for 90min then concentrated NH3 (5ml) was added drop-wise. The mixture was warmed up to room temperature over 30min, filtered through Celite filter agent, washed with methanol and the filtrate was concentrated in vacuo. The residue was purified by flash chromatog­raphy on silica gel (eluant; 1% 35% ammonia:10% metha­nol: 89% dichloromethane) to yield the title compound (670mg, 37%) .

The synthetic route of Methyl 4-cyano-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRING B.V.; WO2006/21213; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 25978-68-1, 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 25978-68-1 as follows.

To a solution of methyl 4-cyano-3-methylbenzoate (36 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) and water (0.500 mL), was added sodium hydrogen sulfide (0.019 mL, 0.616 mmol) and triethylamine hydrochloride (170 mg, 1.233 mmol). The reaction mixture was heated at 55 0C overnight. The reaction was allowed to cool and water was added. The mixture was extracted with EtOAc. The combined organic layers were dried (Na2SC^), filtered and the solvent was evaporated in vacuo to give the product as a yellow solid. LCMS calc. = 210.1; found = 210.2 (M+l)+. 1H NMR (500 MHz, CDCl3) 7.86 (s, 1 H); 7.84 (d, J = 8.1 Hz, 1 H); 7.42 (d, J= 7.9 Hz, 1 H); 7.16 (s, 2 H); 3.93 (s, 3 H); 2.51 (s, 3 H).

According to the analysis of related databases, 25978-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts