Category: 874-89-5

Electric Literature of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, 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.

A solution of 25.0 g (150 mmol) of 4- (hydroxymethyl) benzonitrile, 20.8 g (300 mmol) of hydroxyamine hydrochloride and 50.4 g (600 mmol) of sodium bicarbonate in 250 [ML] of methanol was heated to reflux and stirred for 20 h. The reaction mixture was cooled to rt and filtered. The solid was washed with 100 mL of methanol. The combined methanol solution was concentrated to dryness to afford [31.] 0 g (99 %) of the title compound: 1H NMR (400 Mhz, CD30D) [8] 4.63 (s, 2H), 7.39 (d, J= 8.0, 2H), 7.62 (d, J= 8.0, 2H).

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Hydroxymethyl)benzonitrile

Synthesis was performed using a PE Biosystems (Applied Biosystems) Solaris 530 organic synthesizer. 4-Cyanobenzyl alcohol (0.6 mmol) was dissolved in 3 mL DMA then transferred to a 4 mL vial containing 0.5 mmol of Dess-Martin Reagent. The vial was shaken to ensure mixing then used directly. A round bottom flask was charged with 3 equivalents of MP-BH3CN. The block was placed on the Solaris 530 and 1 equivalent of 5-(4-amino-phenyl)-6-ethyl-pyrimidine-2,4-diamine from Example 1C (dissolved in 1:1 MeOH/CH2Cl2) was added to the round bottom flask. The oxidized 4-cyanobenzyl alcohol was then added (2 eq) followed by 3 equivalents of a solution of HOAc in 1:1 MeOH/CH2Cl2. The block was then heated to 55C overnight. The mixture was transferred with MeOH to a 20 mL vial containing scavenger resins PS-TsNHNH2 and MP-Carbonate (3 eq each). The resins were filtered and the product concentrated. Purification by Reverse Phase HPLC to provided the titled compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 0.94 (t, J=7.49 Hz, 3H), 2.11 (q, J=7.59 Hz, 2H), 4.38 (d, J=5.93 Hz, 2 H), 5.32 (s, 2H), 5.77 (s, 2H), 6.44 (t, J=5.93 Hz, 1H), 6.61 (d, J=8.42 Hz, 2 H), 6.85 (d, J=8.42 Hz, 2H), 7.58 (d, J=8.11 Hz, 2H), 7.80 (d, J=8.11 Hz, 2H);MS (ESI) positive ion 345(M+H)+.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kosogof, Christi; Liu, Bo; Liu, Gang; Liu, Mei; Nelson, Lissa T. J.; Serby, Michael D.; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; US2005/171131; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 874-89-5, These common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, 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.

Preparation of Intermediate 2 (Int.2); N’-Hydroxy-4-(hydroxymethyl)benzimidamide; [00110] A solution of 4-(hydroxymethyl)benzonitrile (22.43g, 0.1685g), hydroxylamine hydrochloride (18.67g, 0.2689 mol) and NaHCO3 (45.22g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ~75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N’-hydroxy-4- (hydroxymethyl)benzimidamide (28.5g) as a white solid. The material was used without further purification. The compound had an HPLC retention time = 0.232 min. – Column: CHROMOLITH SpeedROD 4.6 x 50 mm (4 min.); Solvent A = 10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B = 90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1 = 167.3

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric, J.; PITTS, William, J.; WATTERSON, Scott, Hunter; WO2010/85584; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., 874-89-5

EXAMPLE 6 4-({[4-(2,4-Diamino-6-ethylpyrimidin-5-yl)phenyl]amino}methyl)benzonitrile Synthesis was performed using a PE Biosystems (Applied Biosystems) Solaris 530 organic synthesizer. 4-Cyanobenzyl alcohol (0.6 mmol) was dissolved in 3 mL DMA then transferred to a 4 mL vial containing 0.5 mmol of Dess-Martin Reagent. The vial was shaken to ensure mixing then used directly. A round bottom flask was charged with 3 equivalents of MP-BH3CN. The block was placed on the Solaris 530 and 1 equivalent of 5-(4-amino-phenyl)-6-ethyl-pyrimidine-2,4-diamine from Example 1C (dissolved in 1:1 MeOH/CH2Cl2) was added to the round bottom flask. The oxidized 4-cyanobenzyl alcohol was then added (2 eq) followed by 3 equivalents of a solution of HOAc in 1:1 MeOH/CH2Cl2. The block was then heated to 55C overnight. The mixture was transferred with MeOH to a 20 mL vial containing scavenger resins PS-TsNHNH2 and MP-Carbonate (3 eq each). The resins were filtered and the product concentrated. Purification by Reverse Phase HPLC to provided the titled compound. 1H NMR (500 MHz, DMSO-d6) delta ppm 0.94 (t, J=7.49 Hz, 3 H), 2.11 (q, J=7.59 Hz, 2 H), 4.38 (d, J=5.93 Hz, 2 H), 5.32 (s, 2 H), 5.77 (s, 2 H), 6.44 (t, J=5.93 Hz, 1 H), 6.61 (d, J=8.42 Hz, 2 H), 6.85 (d, J=8.42 Hz, 2 H), 7.58 (d, J=8.11 Hz, 2 H), 7.80 (d, J=8.11 Hz, 2 H); MS (ESI) positive ion 345(M+H)+.

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; Kosogof, Christi; Liu, Bo; Liu, Gang; Liu, Mei; Nelson, Lissa T.J.; Serby, Michael D.; Sham, Hing L.; Szczepankiewicz, Bruce G.; Xin, Zhili; Zhao, Hongyu; US2005/70712; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., 874-89-5

a 2-Chlorobenzenesulfonic acid 3-[(4-cyanophenyl)methoxy]-5-methylphenyl ester Diethyl azodicarboxylate (524 mg, 3.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester (900 mg, 3.0 mmol), as prepared in step (c) of the Example 1, 4-cyanobenzyl alcohol (400 mg, 3.0 mmol; Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (790 mg, 3.0 mmol) in tetrahydrofuran (20 mL) at 0 C. The mixture was stirred at 0 C. for 2 h and at room temperature for 3 h. The reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (3*50 mL). The organic phase was washed sequentially with saturated NaHCO3 (2*50 mL) and brine (2*50 mL), and dried over Na2 SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a white solid (0.95 g, 76%). 1 H-NMR (300 MHz, CDCl3) delta 2.26 (s, 3H), 5.03 (s, 2H), 6.57 (t, 1H, J=2.2 Hz), 6.59 (s, 1H), 6.67 (s, 1H), 7.38 (t, 1H, J=5.8 Hz), 7.49 (d, 2H, J=4.2 Hz), 7.60 (m, 2H), 7.67 (d, 2H, J=3.5 Hz) and 7.96 (d, 1H, J=3.6 Hz).

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; 3-Dimensional Pharmaceuticals, Inc.; US6034127; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 874-89-5 as follows. 874-89-5

Example 99 N-((4-(hydroxymethyl)phenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide hydrochloride (57MBT72D) To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0 C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2) gave 152 mg (29%) of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30% MeOH in CH2Cl2+3.5% NH4OH).

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACADIA Pharmaceuticals Inc.; ANDERSSON, Carl-Magnus A.; CROSTON, Glenn; HANSEN, Eva Louise; ULDAM, Allan Kjaersgaard; US2015/259291; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts