Category: 7664-66-6

Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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. Safety of 4-Isopropoxyaniline

Synthesis of compound 126.1. To a solution of 2.5 (0.30 g, 0.96 mmol, 1.0 eq) in dry CH3CN (5mL) were added 4-isopropoxyaniline (0.145g, 0.96mmol, l .Oeq), and DIPEA (0.49 mL, 2.88 mmol, 3. Oeq). Reaction mixture was allowed to stir at 100 C for 24 hours. After completion of the reaction, the mixture was cooled to room temperature. Water (10 mL) was added to the mixture and extracted with EtOAc. Organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give crude which was purified by column chromatography to afford compound 126.1 (0.300g, 73.15%). MS (ES): m/z = Ml A [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7664-66-6, its application will become more common.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
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7664-66-6, name is 4-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 4-Isopropoxyaniline

Into a stirringmixture of ethyl acetate (20 mL), tetrahydrofuran (4 mL), water(4 mL), sodium carbonate (0.8 g, 7.9 mmol, 0.6 equiv.), and 4-isopropoxyaniline (2.0 g, 13.2 mmol, 1 equiv.), phenyl chloroformate(2.3 g, 14.5 mmol, 1.1 equiv.) was added dropwise at 0 C.The reaction was stirred at room temperature overnight, then itwas evaporated under reduced pressure and the resultant wasadded into 20 mL water, the precipitate was filtered and washedwith water, then dried under vacuum to afford 3.2 g of 13a as whitesolid; yield: 90%; MS (ESI) m/z: 286.1 [MH], 308.1 [MNa].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yingxiu; Ye, Tianyu; Xu, Le; Dong, Yuhong; Luo, Yong; Wang, Chu; Han, Yufei; Chen, Ke; Qin, Mingze; Liu, Yajing; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

7664-66-6, name is 4-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 4-Isopropoxyaniline

Into a stirringmixture of ethyl acetate (20 mL), tetrahydrofuran (4 mL), water(4 mL), sodium carbonate (0.8 g, 7.9 mmol, 0.6 equiv.), and 4-isopropoxyaniline (2.0 g, 13.2 mmol, 1 equiv.), phenyl chloroformate(2.3 g, 14.5 mmol, 1.1 equiv.) was added dropwise at 0 C.The reaction was stirred at room temperature overnight, then itwas evaporated under reduced pressure and the resultant wasadded into 20 mL water, the precipitate was filtered and washedwith water, then dried under vacuum to afford 3.2 g of 13a as whitesolid; yield: 90%; MS (ESI) m/z: 286.1 [MH], 308.1 [MNa].

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yingxiu; Ye, Tianyu; Xu, Le; Dong, Yuhong; Luo, Yong; Wang, Chu; Han, Yufei; Chen, Ke; Qin, Mingze; Liu, Yajing; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, 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.

The compound obtained in Reference Example 1-2 (19mg) and 4-isopropoxyaniline (10mg) was dissolved in acetonitrile (1.5 mL). And reacted for 10 minutes at the microwave irradiation under 180 C. After the solvent was concentrated to give the title compound purified by silica gel column chromatography (17mg, 60%).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
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Ether | (C2H5)2O – PubChem

Electric Literature of 7664-66-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 7664-66-6 name is 4-Isopropoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The compound obtained in Step 5 (19 mg) was dissolved in dioxane (1 mL), 4 isopropoxyphenylaniline (12mg) and 4N hydrochloric acid dioxane (64muL), and the mixture was stirred for 20 minutes in a microwave irradiation under 180 . The reaction solution was extracted three times with chloroform after adding a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was concentrated after dried over sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (13mg, 57%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H13NO

Phenyl chloroformate (15.2 kg, 97.1 mol) was dissolved in toluene (115.7 kg) and cooled to 3 0C. 4-isopropoxyaniline (III) (13.3 kg, 88.0 mol) was mixed with acetonitrile (43.4 kg) and slowly added to the phenyl chloroformate solution over 1 hour 40 minutes, followed by slow addition of triethylamine (9.8 kg, 96.8 mol) over 46 minutes. The mixture was heated to 17.5 0C and stirred for 3 hours 30 minutes until the reaction was deemed complete by HPLC. The product solution was washed with IN HCl, followed by removing acetonitrile though an azeotropic distillation with additional toluene (52.3 kg). The solution was heated to 58 0C before slowly adding heptane (43.7 kg) over 1 hour 2 minutes, after which the slurry was cooled to 23.5 0C over 2 hours 35 minutes and stirred for an additional 2 hours 51 minutes. The material was isolated, washed twice with heptane, and dried at < 40 0C for 3 hours 49 minutes. The product was discharged, yielding 19.1kg of the title compound (HIa) (80% yield, 100% purity HPLC AUC). 1H NMR (300 MHz, CD3OD, delta): 7.38 (m, 4H), 7.19 (m, 3H), 6.86 (d, J = 9Hz 2H), 4.52 (sept, J = 6Hz, IH), 1.28 (d, J = 6Hz, 6H). 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 7664-66-6. Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC; ARMITAGE, Ian; BOURLAND, Michael, E.; BOYLE, Craig, J.S.; COOPER, Martin, Ian; FERDOUS, Abu, J.; LANGSTON, Marianne; WO2010/59239; (2010); A2;,
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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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Isopropoxyaniline

Step 1 (4-isopropoxyphenyl)hydrazine hydrochloride To a stirred solution of 4-(propan-2-yloxy)aniline (5.0 g, 33.07 mmol, 1.00 equiv) in 2N hydrochloric acid (35 mL) at 0 C. was added dropwise a solution of sodium nitrite (2.4 g, 34.78 mmol, 1.05 equiv) in water (8 mL). The reaction mixture was stirred at 0-5 C. for 1 h. A solution of SnCl2.H2O (15 g, 66.37 mmol, 2.01 equiv) in 12N hydrochloric acid (20 mL) was then added dropwise at 0-5 C. The resulting mixture was stirred at room temperature overnight. The precipitates was collected by filtration to give 4.7 g (70%) of crude (4-isopropoxyphenyl)hydrazine hydrochloride as a purple solid. The product was used in the next step without further purification.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Chesworth, Richard; Mitchell, Lorna Helen; Shapiro, Gideon; US2014/315961; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem