Heterocyclic Building Blocks-benzodioxan

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO61,mainly used in chemical industry, its synthesis route is as follows.,17413-10-4

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 complex challenges of chemical substances, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)methanamine,belong benzodioxans compound

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4442-54-0,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,as a common compound, the synthetic route is as follows.

1, 4 – benzene and dioxane -6 – formic acid (25.0g, 139mmol) dissolved in methanol (180 ml) in, concentrated sulfuric (17.5 ml), heated to 70 ¡ãC stirring 5 hours. Cooling to room temperature, concentrated under reduced pressure, for 5percent of sodium hydroxide aqueous solution to adjust the pH to the alkaline, extracted with ethyl acetate, dried, concentrated to obtain 1, 4 – benzene and dioxane -6 – methyl formate (white solid 26.8g, 99percent)., 4442-54-0

4442-54-0 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid 2758833, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Patent; Shanghai Huilun Life Technology Co., Ltd.; Cheng Jianjun; Qin Jihong; (25 pag.)CN104557955; (2017); B;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid, cas is 4442-54-0, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,4442-54-0

1,4-Benzodioxane-6-carboxylic acid (4.5g, 25 mmol) was refluxed in thionyl chloride (25ml) for 3hr, the solution was then evaporated to dryness to give l,4-benzodioxin-6- carbonyl chloride as a pale solid 4.9g (yield: 100percent).

With the rapid development of chemical substances, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid

Reference£º
Patent; TRAGEX PHARMA; HADJ-SLIMANE, Reda; GARBAY, Christiane; WO2012/156289; (2012); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Name is 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid, as a common heterocyclic compound, it belongs to benzodioxans compound, and cas is 3663-80-7, its synthesis route is as follows.,3663-80-7

To a solution of Example 23B (40mg, 0.140 mmol) in N,N-dimethylformamide (0.8 mL) were added 2,3-dihydrobenzo[Z?][l ,4]dioxine-2-carboxylic acid (27.8 mg, 0.155 mmol), 1- [bis(dimethylamino)methylene]- lH-l,2,3-triazolo[4,5- ?]pyridinium 3-oxid hexafluorophosphate (HATU, 58.8 mg, 0.155 mmol), and NN-diisopropylethylamine (0.074 mL, 0.421 mmol) at room temperature. The reaction mixture was stirred for 1 hour at room temperature. The mixture was purified by preparative HPLC [Waters XB ridge? C18 5 muiotaeta OBD? column, 30 x 100 mm, flow rate 40 mL/minute, 5-100percent gradient of acetonitrile in buffer (0.1 percent trifluoroacetic acid in water)] to give the title compound.(45mg, 0.101 mmol, 71.7 percent yield). H NMR (501 MHz, DMSO-ifc) delta ppm 8.78 (s, 1H), 8.70 (s, 1H), 7.47 (t, J = 8.9 Hz, 1H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 6.97 – 6.92 (m, 1H), 6.87 – 6.80 (m, 4H), 4.67 (dd, J = 6.5, 2.7 Hz, 1H), 4.45 (s, 2H), 4.31 (dd, J = 11.6, 2.7 Hz, 1H), 4.12 (dd, J = 11.6, 6.5 Hz, 1H), 2.24 (s, 6H); MS (ESI+) m/z 464 (M+NH4)+.

With the complex challenges of chemical substances, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid

Reference£º
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; CHUNG, Seungwon; ZHANG, Qingwei, I.; SHI, Lei; MURAUSKI, Kathleen; DART, Michael, J.; RANDOLPH, John, T.; (238 pag.)WO2019/90085; (2019); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4442-54-0,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,as a common compound, the synthetic route is as follows.

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.14 (3-(4-Bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (C14) White crystal, mp: 140-141 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.23-3.29 (d, J = 17.1 Hz, 1H), 3.80-3.87 (m, 1H), 4.35-4.37 (t, J = 3.9 Hz, 4H), 5.63-5.69 (m, 1H), 6.90-6.96 (m, 2H), 7.11 (m, 1H), 7.33-7.35 (d, J = 6.6 Hz, 1H), 7.47-7.50 (m, 4H), 7.59 (s, 1H), 7.66-7.69 (d, J = 8.4 Hz, 2H). MS (ESI): 481.05 (C24H19BrFN2O3, [M+H]+). Anal. Calcd for C24H18BrFN2O3: C, 59.89; H, 3.77; Br, 16.60; F, 3.95; N, 5.82; O, 9.97. Found: C, 59.72; H, 3.74; N, 5.82., 4442-54-0

As the paragraph descriping shows that 4442-54-0 is playing an increasingly important role.

Reference£º
Article; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid, cas is 4442-54-0, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,4442-54-0

General procedure: The benzoic acid was mixed with SOCl2. The mixture was heated at reflux for 2 h. The solvent was evaporated in vacuo. The solid was dissolved in DCE (20 mL) and the mixture was concentrated in vacuo. This afforded the acid chloride, which was immediately used in the crude form.

With the rapid development of chemical substances, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid

Reference£º
Article; Wijtmans, Maikel; Maussang, David; Sirci, Francesco; Scholten, Danny J.; Canals, Meritxell; Mujic?-Delic?, Azra; Chong, Milagros; Chatalic, Kristell L.S.; Custers, Hans; Janssen, Elwin; De Graaf, Chris; Smit, Martine J.; De Esch, Iwan J.P.; Leurs, Rob; European Journal of Medicinal Chemistry; vol. 51; (2012); p. 184 – 192;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid, and cas is 3663-80-7, its synthesis route is as follows.,3663-80-7

Compound 1 was prepared according to Scheme 5, shown below. The coupling of 2,3-dihydrobenzo[b][l ,4]dioxine-2-carboxylic acid and hydrazinecarbothioamide via an addition reaction and subsequent dehydration was performed in the presence of hydroxybenzotriazole (HOBt), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and triethylamine (TEA) dissolved in tetrahydrofuran (THF). A cyclization reaction of 2- (2,3-dihydrobenzo[b][l,4]dioxine-2-carbonyl)hydrazinecarbothioamide was performed in an aqueous solution of NaOH (95percent) to afford the thiol intermediate. Finally, the ttle compound was formed by treating the thiol with sulfuric acid in acetic acid.

With the complex challenges of chemical substances, we look forward to future research findings about 3663-80-7,belong benzodioxans compound

Reference£º
Patent; THE GENERAL HOSPITAL CORPORATION; ZAPOL, Warren M.; BLOCH, Kenneth D.; NAKAGAWA, Akito; LUI, Francine E.; FREEDMAN, Revital; WO2015/106240; (2015); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is Methyl 1,4-Benzodioxan-6-carboxylate, and cas is 20197-75-5, its synthesis route is as follows.,20197-75-5

Step B Preparation of 6-nitro-3,4-ethylenedioxybenzoic acid methyl ester To a solution of 5.0 g. of 3,4-ethylenedioxybenzoic acid methyl ester in 5.0 mls. of glacial acetic acid is added dropwise 5.0 mls. of 70percent nitric acid at 50¡ã-60¡ãC. After addition the reaction mixture is kept at 55¡ãC. for one hour, then cooled and 50 mls. of ice water added. The resulting precipitate is recovered by filtering, water washed and dried to obtain 6-nitro-3,4-ethylenedioxybenzoic acid methyl ester, m.p. 115¡ã-118¡ãC.

With the complex challenges of chemical substances, we look forward to future research findings about 20197-75-5,belong benzodioxans compound

Reference£º
Patent; Sandoz Inc.; US3931179; (1976); A;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid, cas is 4442-53-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,4442-53-9

6,7-dibromo-1,4 -benzodioxane-5-carboxylic acid 1,440 ml of acetic acid and 360 g of 1,4-benzodioxane-5-carboxylic acid were introduced into a balloon flask provided with an agitator, an introduction funnel and a condenser. The mixture was heated to 55¡ã C. and then a solution of 700 g of bromine in 360 ml of acetic acid was added in portions. The mixture was heated to 120¡ã C. and then cooled to 15¡ã C. The precipitate was dried off, washed with acetic acid and dried. 332 g of 6,7-dibromo-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 212¡ã C.). The structure was confirmed by nuclear magnetic resonance analysis.

4442-53-9 is used more and more widely, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Reference£º
Patent; Societe D’Etudes Scientifiques et Industrielles de L’ile-de-France; US4186135; (1980); A;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Name is 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid, as a common heterocyclic compound, it belongs to benzodioxans compound, and cas is 3663-80-7, its synthesis route is as follows.,3663-80-7

To a solution of 5-chloro-lH-indole-2-carboxylic acid hydrazide (Preparation 1, 0. 50g, 2. 39mmol) in DMF (5rnL) was added HOBt (0. 32g, 2. 39mmol), DIPEA (0.83mL, 4. 78mmol) and 2,3-dihydrobenzo [1, 4] dioxine-2-carboxylic acid (0.43g, 2.39mmol) followed by EDCI (0. 55g, 2. 87mmol). The reaction mixture was stirred at rt for 16h, poured into water (75mL) and extracted with ethyl acetate (2 x 150mL). The combined organic extracts were washed with HCl (IN, 50mL), NaOH (1N, 50mL) and saturated sodium chloride solution (75mL). The organic layer was dried (MgS04) and concentrated in vacuo to give the title compound. m/z (ES+) = 372 [M+ H] + ; RT = 3. 57min.

With the complex challenges of chemical substances, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid

Reference£º
Patent; PROSIDION LIMITED; WO2005/85194; (2005); A2;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem