Month: August 2020

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid,4442-53-9,Molecular formula: C9H8O4,mainly used in chemical industry, its synthesis route is as follows.,4442-53-9

Example 81a (S)-ethyl 4-amino-5-(2-(2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamido)-propoxy)-2-methylquinoline-3-carboxylate Prepared as in Example 24a from (S)-ethyl 4-amino-5-(2-aminopropoxy)-2-methyl-quinoline-3-carboxylate (Example 26b) and 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid as brown solid. MS 466 (MH+).

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid,belong benzodioxans compound

Reference£º
Patent; SENOMYX, INC.; US2012/41078; (2012); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO431,mainly used in chemical industry, its synthesis route is as follows.,4442-53-9

A 20-mL round bottom flask was charged with 2,3-dihydrobenzo[b][l,4]dioxine- 5-carboxy-lic acid (1.8 g, 1.0 mmol), bromine (3.16 g, 2.0 mmol), and acetic acid (2 mL). The reaction mixture was stirred at 120¡ãC for 2 h and then cooled to 15¡ãC. It was filtered and the solid was washed with acetic acid to afford the title compound as a white solid (3.0 g, 60percent). LCMS: ESI (3 minute run), m/z = 337 [M+l]+; Retention time: 1.21 minute.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid,belong benzodioxans compound

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BAKER-GLENN, Charles; BURDICK, Daniel Jon; CHAMBERS, Mark; CHAN, Bryan K.; CHEN, Huifen; ESTRADA, Anthony; GUNZNER-TOSTE, Janet; SHORE, Daniel; SWEENEY, Zachary; WANG, Shumei; ZHAO, Guiling; WO2013/79494; (2013); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oxime,31127-39-6,Molecular formula: C9H9NO3,mainly used in chemical industry, its synthesis route is as follows.,31127-39-6

General procedure: A solution of a respective oxime 2a,b or 5a,b (18 mmol) in acetic anhydride (10 mL) was heated to reflux for 8-12 h. Afterwards, the solvent was then removed in vacuo, the residue was quenched by adding cold water (10 mL), and keeping the temperature of the resulting mixture at 15-20C for 1-2 h. The formed precipitate was isolated, and dried at 40oC to give title compounds 3a,b or 6a,b, respectively.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oxime,belong benzodioxans compound

Reference£º
Article; Le-Nhat-Thuy, Giang; Dinh, Thuy Van; Pham-The, Hai; Nguyen Quang, Hung; Nguyen Thi, Nga; Dang Thi, Tuyet Anh; Hoang Thi, Phuong; Le Thi, Tu Anh; Nguyen, Ha Thanh; Nguyen Thanh, Phuong; Le Duc, Trung; Nguyen, Tuyen Van; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3741 – 3747;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO436,mainly used in chemical industry, its synthesis route is as follows.,31127-39-6

General procedure: A mixture of a’ (10.0 mmol) in CH2Cl2 was stirred at room temperature, NCS (1.60 g, 12.0 mmol) was then added. The resulted mixture was stirred at reflux and propynol (0.56 g, 10.0 mmol) was added dropwise. After 0.5 h, triethylamine (1.01 g, 10 mmol) was added dropwise and refluxed for another 4 h. After cooling, the reaction mixture was washed with water and evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography with petroleum ether/ethyl acetate as eluent to give intermediate b’.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oxime,belong benzodioxans compound

Reference£º
Article; Niu, Chao; Yin, Li; Nie, Li Fei; Dou, Jun; Zhao, Jiang Yu; Li, Gen; Aisa, Haji Akber; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5440 – 5448;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO421,mainly used in chemical industry, its synthesis route is as follows.,31127-39-6

General procedure: From exo-glucal 3A. An aqueous solution of NaOCl (5 mL, 9Chl prepared from a 36Chl commercial solution, diluted 4 times) was added slowly with a syringe pump (~16 h) at rt to a solution of methylene exo-glycal 3A (100 mg, 0.29 mmol) and aldoxime (0.58 mmol, 2 eq) in THF (10 mL). The mixture was diluted withwater (10 mL) and extracted with CH2Cl2 (3 20 mL). The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography (petroleum ether/EtOAc, 7:3) to afford the corresponding spiro-isoxazolines 4a,f-j,l-p.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oxime,belong benzodioxans compound

Reference£º
Article; Goyard, David; Konya, Balint; Chajistamatiou, Aikaterini S.; Chrysina, Evangelia D.; Leroy, Jeremy; Balzarin, Sophie; Tournier, Michel; Tousch, Didier; Petit, Pierre; Duret, Cedric; Maurel, Patrick; Somsak, Laszlo; Docsa, Tibor; Gergely, Pal; Praly, Jean-Pierre; Azay-Milhau, Jacqueline; Vidal, Sebastien; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 444 – 454;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde,29668-44-8,Molecular formula: C9H8O3,mainly used in chemical industry, its synthesis route is as follows.,29668-44-8

25 g of the product of Example 1,Adding 500 mL of water to raise the temperature to 70-80 DEG C,Then, 30 g of KMnO4 + 500 mL of an aqueous solution was prepared,Dropping into the above reaction solution, heating for 40 minutes and heating to reflux for 2 hours,The reaction was terminated by TLC, cooled to room temperature, alkalified by addition of 10percent aqueous KOH,Filter cake washed with water to neutral, the filtrate acidified with concentrated hydrochloric acid,A large amount of white solid was precipitated, and the filter cake was washed with water and dried to obtain 23 g of a white solid in 90percent yield.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde,belong benzodioxans compound

Reference£º
Patent; Shanghai PharmValley Corp.; Yu, Weiyong; Yang, Ling; Wang, Ailing; (4 pag.)CN105801556; (2016); A;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO385,mainly used in chemical industry, its synthesis route is as follows.,29668-44-8

Example-8Preparation of 2,3-dihydro-benzo[1,4]dioxin-6-yl-methylamine hydrochloride 242.0 g of Methanolic ammonia [as 100% w/w by chemical assay] [Note: as chemical assay: 23.0% w/w, volume 1350.0 ml] and 30.0 g (0.183 mol) of 1,4-benzodioxan-6-carboxaldehyde were charged into a 2.0 L 4 necked round bottom flask, connect to a mechanical stirrer, thermo meter socket and condenser at 20-30 C. Stirred the mass for 20-30 min at 20-30 C. After dissolution is clear. Reaction mass was charged into a 2.0 L hydrogenator kettle at 20-30 C. 30.0 g of Raney Nickel (with Methanol dried) was charged under nitrogen atmosphere. Kettle was fitted to the hydrogenator. Nitrogen atmosphere was removed in Hydrogenator kettle with hydrogen gas by slowly flushing. Hydrogen gas was feeded upto 50-55 psi in hydrogenation kettle under oscillation. Maintained the hydrogen gas pressure (50-55 psi) till the hydrogen gas consumption is stopped. Reaction mass temperature was raised to 40-45 C. After hydrogen gas consumption is stooped at 45-50 C. Reaction mass temperature was cooled to 25-30 C. Maintained the hydrogen gas pressure at 50-55 psi for till the hydrogen gas consumption is stopped (about 90-120 min) Raney nickel was filtered through hyflow bed under nitrogen atmosphere. Raney Nickel was washed with 300.0 ml of methanol under nitrogen atmosphere. Filterate was collected into a flask. Methanol was distilled completely under vacuum at mass temperature not crossing 55 C. Mass temperature was cooled to 40-45 C. and release the vacuum. 50.0 ml of isopropyl alcohol was added. Reaction mass pH was adjusted to 0.5+/-0.25 with IPA HCl. Maintained the mass temperature at 25-30 C. for 60-90 min under stirring. Solid was filtered and solid was washed with 20.0 ml of isopropyl alcohol. Compound was dried under vacuum at 40+/-5 C. Dry compound weight: 31.0 g (yield: 84.1%).Spectral data:FT-IR (K Br) (cm-1): 3447.6, 2977.6, 2870.0, 1594.5, 1506.6, 1474.0, 1285.8, 1077.7, 1051. 735.2, 617.9, 472.0MS: 202.6 [M+1]

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde,belong benzodioxans compound

Reference£º
Patent; Natco Pharma Limited; US2010/298351; (2010); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO360,mainly used in chemical industry, its synthesis route is as follows.,29668-44-8

General procedure: To a mixture of aldehyde 1 (10.0 mmol) in 30% methanol aqueous solution, NH2OH¡¤HCl (0.695 g, 10.0 mmol) was added slowly. After the NH2OH¡¤HCl was fully dissolved, Na2CO3 (0.53 g 5.0 mmol) was added and then the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic phase was dried to afford intermediate 2 as white solids.

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde,belong benzodioxans compound

Reference£º
Article; Pang, Guang Xian; Niu, Chao; Mamat, Nuramina; Aisa, Haji Akber; Bioorganic and Medicinal Chemistry Letters; vol. 27; 12; (2017); p. 2674 – 2677;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,Methyl 1,4-Benzodioxan-6-carboxylate,20197-75-5,Molecular formula: C10H10O4,mainly used in chemical industry, its synthesis route is as follows.,20197-75-5

General procedure: A mixture of 60% NaH (0.12g, 5mmol) was added in anhydrous THF (10mL), followed by the addition of anhydrous CH3CN (0.21g, 5mmol) and compound 2 (0.42g, 2.5mmol) in the ice bath. Reaction was heated to reflux and stirred for 6h. Upon completion, the reaction mixture was taken up in ice water (30mL) and the pH was adjusted to 5. After filtration, the filtrate was extracted with ethyl acetate (20mL¡Á3). The combined organic phase was washed twice with saturated brine (20mL¡Á2) and dried over anhydrous MgSO4. Then, MgSO4 was filtered out, and the filtrate was concentrated in vacuo, Followed by recrystallization of the residue to afford compound 19a as a pale-yellow solid.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 1,4-Benzodioxan-6-carboxylate,belong benzodioxans compound

Reference£º
Article; Heng, Hao; Wang, Zhijie; Li, Hongmei; Huang, Yatian; Lan, Qingyuan; Guo, Xiaoxing; Zhang, Liang; Zhi, Yanle; Cai, Jiongheng; Qin, Tianren; Xiang, Li; Wang, Shuxian; Chen, Yadong; Lu, Tao; Lu, Shuai; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 248 – 267;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belong benzodioxans compound,Methyl 1,4-Benzodioxane-2-carboxylate,3663-79-4,Molecular formula: C10H10O4,mainly used in chemical industry, its synthesis route is as follows.,3663-79-4

General procedure: Methyl 1,4-benzodioxan-2-carboxylate (¡À)-17a was dissolved in ? THF/ ? H2O (1:1 ratio) after which ? lithium hydroxide was added. The reaction was stirred for 3?h until hydrolysis was complete. Next, THF was evaporated and the residue acidified with 10percent HCl. DCM was used for extraction. The organic layers were dried in vacuo to give ? (¡À)-1,4-benzodioxan-2-carboxylic acid 1 in 91percent yield as a white solid; mp 117?119?¡ãC; [lit.23b 125.4]; 1H NMR: delta 4.44 (d, J?=?4.8?Hz, 2H), 4.90 (t, J?=?3.7, 7.6?Hz, 1H), 6.88?6.97 (m, 3H), 6.99?7.02 (m, 1H); 13C NMR: delta 64.63, 71.61, 117.34, 122.38, 141.97, 142.87 173.59; HRMS (ESI) Calcd for C9H8NaO4 (M+Na): 203.0320. Found: 203.0317.

With the synthetic route has been constantly updated, we look forward to future research findings about Methyl 1,4-Benzodioxane-2-carboxylate,belong benzodioxans compound

Reference£º
Article; Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C.; Tetrahedron Asymmetry; vol. 23; 22-23; (2012); p. 1615 – 1623;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem