Category: 213598-11-9

Application of 213598-11-9, A common heterocyclic compound, 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate, molecular formula is C12H13NO3, 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.

To a mixture of methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (27 g, 123.28 mmol) (Description 4) in methanol (150 mL) was added sodium hydroxide (5N) (27 mL, 135 mmol) and the mixture stirred at RT for 16 h. The mixture was then reduced in vacuo and acidified with hydrochloric acid (2M) (35 mL). Ethyl acetate (200 mL) was added, the layers separated and the organic layer dried over sodium sulfate and then reduced to a solid which was washed with pentane to afford the title compound (25.27 g).

The synthetic route of 213598-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BAILEY, James; KING, Nigel Paul; LIN, Xichen; REN, Feng; TAN, Kheng-Chuan; MAK, Sing Yeung; WO2011/72488; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 213598-11-9, 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. 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 3-cyano-4-(propan-2-yloxy) benzoic acid: To a solution of methyl 3-cyano-4- (propan-2-yloxy)benzoate (5 g, 22.81 mmol, 1.00 equiv) in methanol/ water ( 30: 10 mL) was added sodium hydroxide (1.77 g, 2.30 equiv). The resulting solution was stirred for 2 h at 25 C. The pH value of the solution was adjusted to 3 with hydrogen chloride (1 Mol/L). The resulting solution was extracted with ethyl acetate (3 x 20 mL), and the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under vacuum to afford 4.4 g of 3-cyano-4-(propan-2-yloxy) benzoic acid as a white solid.

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, Methyl 3-cyano-4-isopropoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; ZHANG, Chengzhi; CHAKMA, Justin; (91 pag.)WO2016/164180; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 213598-11-9, 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 213598-11-9 as follows.

To a solution of methyl 3-cyano-4-hydroxybenzoate (82 g, 463 mmol; J. Med. Chem, 2002,45, 5769) in dimethylfonnamide (800 mL) was added 2-iodopropane (93 mL, 926 mmol) and potassium carbonate (190 g, 1.4 mol). The resulting mixture was heated at 50 C for 16 h, at which time it was allowed to cool to room temperature. The reaction was filtered and the mother liquor diluted with 0.5 N sodium hydroxide (1 L). The resulting mixture was extracted with ether (2 x I L) and the organics washed with 1 N HCI (1 L) and brine (700 mL), dried (MgSO4) and concentrated to give 100 g (-100%) of methyl 3-cyano-4- [(1-methylethyl) oxy]benzoate as a yellow solid. 3-Cyano-4-[(1-methylethyl)oxy]benzoic acid: [00392] To a cooled (0 C) solution of methyl 3-cyano-4-[(1-methylethyl)oxyJbenzoate (100 g, 463 mmol) in tetrahydrofuran (500 mL) was added 10% potassium hydroxide (500 mL). The resulting solution was allowed to warm to room temperature and maintained for 16 h, at which time it was concentrated to remove the tetrahydrofuran. The residue was diluted with water (500 mL) and washed with ether (2 x 500 mL). The aqueous layer was then acidified with 3 N HCI and stood for 2 h. The solids were collected by filtration and washed several times with water, then dissolved in methylene chloride (1 L). The mostly homogeneous mixture was filtered through Celite and concentrated to a minimal volume of methylene chloride. Collection ofthe solids by filtration gave 82 g (87%) of 3-cyano-4-[(1- methylethyl)oxy]benzoic acid as a white solid. Scheme B: Reagents and Conditions: a) 4N HCI/dioxane, rt; b) HBTU, i-Pr2NEt, DMF, rt; c) 1- ethoxyvinyltn-n-butyltin, PdCh(PPh3)2, dioxane, 100 C; d) NBS, THF/HzO (3:1), rt; e) 2- amino-3-picoline, NaHC03, i-PrOH, 80 C . (3tS)-3-Amino-4-(4-bromophenyl)-1 -butane. hydrochloride. [00393] 1,1-Dimethylethyl {(I S)-l-[( 4-bromophenyl)methyl]-3- hydroxypropyl}carbamate (4.4 g, 12.8 mmol) was dissolved in 4N HCl/dioxane (20 mL). After 2 h, the reaction mixture was concentrated in vacuo to give 3.69 g (94%) of the title compound as a white solid. LC/MS (ES) m/e 244.0 (M + H)+. N- {( 1 S)- I -[ (4-Bromophenyl)methyl]-3-hydroxypropyl }-3-cyano-4-[(1- methylethyl)oxy]benzamide. [00394] To a suspension of (3S)-3-Amino-4-(4-bromophenyl)-1-butanol hydrochloride (1.80 g, 6.42 mmol) in dry DMF (32 mL) was added N, N-diisopropylethyl amine (2.49 g, 19.3 mmol) and the resultant clear solution was stirred for 3 min. 3-Cyano-4-[(1- methylethyl) oxy]benzoic acid (1.45 g, 7.06 mmol) and HBTU (2.68 g, 7.06 mmol) were added and the reaction was stirred at rt under nitrogen. After 1.5 h, the reaction mixture was quenched with water (50 mL) and extracted with EtOAc (3 X 30 mL). The extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (75% EtOAc/hexanes) to give 2.18 g (78%) of the title compound as a white solid. LC/MS (ES) m/e 431.2 (M + H)+. N-«(1S)-I- {[ 4-(Bromoacetyl)phenyl]methyl }-3-hydroxypropyl)-3-cyano-4-[(1- methylethyl) oxy]benzamide. [00395] A flask, dried with a heat gun under argon purge, was charged with N-{(1S)-1- [(4-bromophenyl)methyl]-3-hydrox5propyl}-3-cyano-4-[(1-methylethyl)oxy]benzamide (1.0 g, 2.32 mol). dichlorobis(triphenylphosphine)-palladium(II) (81 mg, 0.116 mol), tributyl(1- ethoxyvinyl) tin (1.68 g, 4.64 mmol), and 1,4-dioxane (15 mL). The mixture was stirred at 100 C for 2 hours under argon. Upon completion, as monitored by LCMS, the reaction was concentrated under reduced pressure and the residue was purified immediately on deactivated silica gel (65% EtOAc/hexanes with 5% triethylamine) to give 720 mg (1.70 mmol) of enol ether intennediate as a colorless foam which was immediately dissolved in THF:H20 (3: 1, 18 mL) and treated with N-bromosuccinimide (3 IS mg, 1.79 mmol). After 15 min at rt, the reaction mixture was concentrated under reduced pressure and the crude residue was diluted with EtOAc (30 mL), washed with biine (10 mL) and water (10 mL) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (80% EtOAc/hexanes) to give 651 mg (59%) of N-«(lS)-I- {[ 4-(bromoacetyJ)phenyl)methyl}-3- hydroxypropyl)-3-cyano-4-[(l -methylethyl)oxy]benzamide as a white tacky solid. LC/MS (ES) m/e 473.2 (M + H)+. 3-Cyano-N ((1S'(at)-3-hydroxy-1-{[(at)4-(8-methylimidazo[1,2-a]p(at)a-idin-2- yl)phenyl ] methj/I ) propyl)-4-[ ( 1 -methyl ethyl)oxy]benzamide. [00396] To a solution of N-( (1 S)-l- {[ 4-(bromoacetyl)phenyl]methyl }-3- hydroxypropyl)-3-cyano-4-[(1-methylethyl)oxy]benzamide (300 mg, 0.634 mmol) in i-PrOH (6 mL) was added 2-amino-3-picoline (Aldrich, 69 mg, 0.634 mmol) followed by solid NaHCO3 (64 mg, 0.761 mmol). The resultant suspension was heated to 80 C. After 7 h, a majority of the i-PrOH was removed under reduced pressure and the residue was dissolved in 3% MeOH/EtOAc (30 mL) and washed with water (10 mL) and brine (10 mL). The combined aqueous layers were extracted with 3% MeO…

According to the analysis of related databases, 213598-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOKINETICS, INC.; SMITHKLINE BEECHAM CORPORATION; WO2005/107762; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 213598-11-9,Some common heterocyclic compound, 213598-11-9, name is Methyl 3-cyano-4-isopropoxybenzoate, molecular formula is C12H13NO3, 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.

4) 50L reaction kettle to add the previous step crude,2N sodium hydroxide (5 L), tetrahydrofuran (2 L) and stirred at 60 C for 1 hourTime. After cooling to room temperature, the mixture was extracted by intermittent stirring, the aqueous solution was extracted into the water phase and the ethyl acetate was taken as the organic phase. The extraction temperatureDegree of stirring, the extractant ethyl acetate and 3-cyano-4-isopropoxybenzoic acid aqueous solution contact; compared to the organic phase / aqueous phase =1, extraction temperature 37 , extraction time = 18 minutes, continuous extraction 3 times, the separation of the aqueous phase, the organic phase was distilled off under reduced pressure, analysisA large amount of white solid was obtained to give 1.1 kg of white solid. The yield was 84% in two steps and 98.5% by HPLC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-cyano-4-isopropoxybenzoate, its application will become more common.