Category: 4442-54-0

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of Compound 1, N-(4-methyl-3-nitrophenyl)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide[0001] Oxalyl chloride (1 .40 ml 16.6 mmol) was added dropwise to a solution of 1 ,4- benzodioxane-6-carboxylic acid (2.486 g, 13.80 mmol) and DMF (0.027 ml_, 0.34 mmol) in dry DCM (34 ml_). The reaction mixture was stirred at rt for 3.5 h, and thenconcentrated. The residue was dissolved in DCM and concentrated again. This residue was dissolved in dry DCM (12 mL) and added dropwise to a solution of 4-methyl-3- nitroaniline (2.100 g, 13.80 mmol) and pyridine (2.23 mL, 27.6 mmol) in dry DCM (25 mL). The reaction mixture was stirred at rt for 2 h, and then concentrated. The resulting solid was suspended in MeOH, diluted with water and then isolated by filtration and washed with water to afford the title compound (4.24 g, 98percent) as a pale tan coloured solid. NMR (500 MHz, DMSO) delta 10.39 (s, 1 H), 8.54 (d, J = 2.2 Hz, 1 H), 7.99 (dd, J = 8.4, 2.3 Hz, 1 H), 7.55 (d, J = 2.1 Hz, 1 H), 7.52 (dd, J = 8.4, 2.2 Hz, 1 H), 7.47 (dd, J = 8.4, 0.8 Hz, 1 H), 7.01 (d, J = 8.4 Hz, 1 H), 4.34-4.29 (m, 4H), 2.49 (s, 3H). HRMS (ESI+): calcd for C16H15N2O5 (M + H)+, 315.0976; found 315.0982., 4442-54-0

The synthetic route of 4442-54-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); 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.

Preparation of Compound 181, N-(4-chloro-3-nitrophenyl)-2,3- dihydrobenzo[b][1,4]dioxine-6-carboxamide[00247] Oxalyl chloride (0.141 mL, 1 .665 mmol) was added dropwise to a solution of 1 ,4-benzodioxane-6-carboxylic acid (250 mg, 1 .388 mmol) and DMF (2.69 mu, 0.035 mmol) in dry DCM (7 mL). The reaction was allowed to stir at room temperature for 2 h. The reaction mixture was concentrated, a further portion of dry DCM (7 ml) was added and concentrated again. This residue was re-dissolved in dry DCM (3 + 3 +1 mL) and added drop-wise to a solution of 4-chloro-3-nitroaniline (239 mg, 1 .388 mmol) and pyridine (0.224 mL, 2.78 mmol) in dry DCM (7 mL). The reaction was allowed to stir for 3 h at room temperature. The solvent was removed in vacuo and the resulting residue was suspended in MeOH and a solid precipitated by addition of water. The precipitate was isolated by filtration and washed with water, then dried under high vacuum to afford the title compound as a dark yellow solid (417 mg, 90percent). 1H NMR (500 MHz, DMSO-d6) delta 10.54 (s, 1 H), 8.59 (d, J= 2.5 Hz, 1 H), 8.05 (dd, J = 8.9, 2.5 Hz, 1 H), 7.75 (d, J = 8.9 Hz, 1 H), 7.59 – 7.46 (m, 2H), 7.02 (d, J = 8.4 Hz, 1 H), 4.35 – 4.28 (m, 6H). HRMS (ESI+): calcd for C15H12ClN2O5 (M + H)+, 335.0435; found 335.0437., 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; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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. 4.5.5 (3-(4-Bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (C5) Yellow crystal, mp: 205-207 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.16-3.24 (d, J = 16.2 Hz, 1H), 3.75-3.80 (m, 1H), 3.83 (s, 3H), 4.33-4.34 (t, 4H, J = 2.4 Hz, 4H), 5.77-5.81 (m, 1H), 6.86-6.93 (m, 3H), 7.25-7.28 (m, 2H), 7.43-7.47 (m, 1H), 7.55 (s, 1H), 7.70-7.73 (d, J = 8.1 Hz, 2H), 7.78-7.81 (m, 2H). MS (ESI): 493.07 (C25H22BrN2O4, [M+H]+). Anal. Calcd for C25H21BrN2O4: C, 60.86; H, 4.29; Br, 16.20; N, 5.68; O, 12.97. Found: C, 60.59; H, 4.27; N, 5.70., 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

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.

General procedure: A mixture of commercial carboxylic acid in freshly distilled thionyl chloride is warmed into reflux for 2 h, then cooled to room temperature and evaporated under vacuum to dryness to afford quantitatively corresponding acid chlorides (3). This crude material might be used without further purification. A mixture of these acid chloride (1.0 equiv) and ammonium thiocyanate (1.0 equiv) is heated in refluxing dry acetone for 1h. Then, the mixture is cooled to room temperature, and a solution of benzimidazole in dry acetone is carefully added. The mixture is warmed again for 1 h, then cooled to 0 ¡ãC, and hydrolyzed with ice. The precipitate is washed with cold water and crude material is crystallized into ethanol., 4442-54-0

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

Reference£º
Article; Liu, Wang-Qing; Megale, Valentino; Borriello, Lucia; Leforban, Bertrand; Montes, Matthieu; Goldwaser, Elodie; Gresh, Nohad; Piquemal, Jean-Philip; Hadj-Slimane, Reda; Hermine, Olivier; Garbay, Christiane; Raynaud, Francoise; Lepelletier, Yves; Demange, Luc; Bioorganic and Medicinal Chemistry Letters; vol. 24; 17; (2014); p. 4254 – 4259;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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. 4.5.7 (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone (C7) White crystal, mp: 137-138 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.20-3.26 (d, J = 17.4 Hz, 1H), 3.76-3.81 (m, 1H), 4.33-4.34 (t, J = 2.1 Hz, 4H), 5.76-5.82 (m, 1H), 7.05-7.12 (m, 3H), 7.25-7.28 (m, 2H), 7.45-7.51 (m, 4H), 7.59 (s, 1H), 7.65-7.68 (d, J = 8.1 Hz, 2H). MS (ESI): 403.14 (C24H20FN2O3, [M+H]+). Anal. Calcd for C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72; N, 6.96; O, 11.93. Found: C, 71.31; H, 4.75; N, 6.97.

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
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

A common heterocyclic compound, the benzodioxans compound, name is 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,cas is 4442-54-0, mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

EXAMPLE 120 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester A solution of 19.6 g (109 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (J. Chem. Soc., 3445, 1957) in 400 mL of MeOH containing 4 mL of H2SO4 was refluxed overnight. Sodium bicarbonate (18 g) was added, the solvent was removed and the residue was triturated several times with Et2O. The washes were combined, filtered through anhyd MgSO4 and evaporated to yield 20.7 g of the title compound as a pale yellow oil: mass spectrum (electron impact, m/e): 194.

As the rapid development of chemical substances, we look forward to future research findings about 4442-54-0

Reference£º
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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

Oxalyl chloride (10 mL) is added to 2,3-dihydro-benzo[1 ,4]dioxine-6-carboxylic acid (14.9 g) dissolved in dichloromethane (100 mL). After the addition of N,N-dimethylformamide (0.5 ml_), the mixture is stirred at room temperature overnight and then concentrated. The residue is taken up in dichloromethane (100 ml.) and added to a mixture of nortropinone hydrochloride (10.0 g) and potassium carbonate (12.0 g) in dichloromethane (50 ml_). Then, pyridine (18 ml.) is added and the mixture is stirred at room temperature overnight. The mixture is concentrated and the residue is taken up in dichloromethane and washed with 1 M aqueous hydrochloric acid, 1 M aqueous NaOH solution, and brine. After drying (Na2SO4), the solvent is removed under reduced pressure to yield the title compound. Yield: 17.3 g (75percent of theory) Mass spectrum (ESI+): m/z = 288 [M+H]+

As the rapid development of chemical substances, we look forward to future research findings about 4442-54-0

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; HAMILTON, Bradford, S.; HIMMELSBACH, Frank; PETERS, Stefan; WO2010/23161; (2010); A1;,
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: To a mixture of compound 7 (0.05 g, 0.17 mmol) and the appropriate aromatic carboxylic acid (0.34 mmol) in anhydrous DMF (2 mL) under argon atmosphere, N,N-diisoprpoylethylamine (DIPEA) (0.128 mL, 0.72 mmol) and HATU (0.168 g, 0.442 mmol)were added. The reaction mixture was stirred at rt for 24 h or at 80 ¡ãC for 5 h (for only 8g), and then quenched with water (30 mL).The aqueous layer was extracted with ethyl acetate (3 20 mL) and the combined organic layers were washed with water and brine,dried over anhydrous Na2SO4, filtered, and the solvent wasremoved under reduced pressure. The resultant residue was purified by flash column chromatography, using the appropriate elution system to afford the target compounds 8a-g in pure form. 4.9.7 4-((2-(2,3-Dihydrobenzo[b][1,4]dioxine-6-carboxamido)quinolin-5-yl)oxy)-N-methylpicolinamide (8g) Flash column chromatography was performed using (hexane:ethyl acetate, 2:1 to 1:1 v/v). White solid; yield 35.7percent; mp 107-110 ¡ãC; 1H NMR (300 MHz, CDCl3) delta 8.81 (br. s, 1H), 8.55 (d, J = 9.2 Hz, 1H), 8.42 (d, J = 5.6 Hz, 1H), 8.28 (d, J = 9.3 Hz, 1H), 8.01 (d, J = 4.4 Hz, 1H), 7.75-7.75 (m, 2H), 7.66 (t, J = 7.6 Hz, 1H), 7.55 (d, J = 2.1 Hz, 1H), 7.49 (dd, J = 8.4, 2.2 Hz, 1H), 7.13 (dd, J = 7.5, 0.8 Hz, 1H), 7.01 (dd, J = 5.6, 2.6 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H), 4.33 (d, J = 2.6 Hz, 4H), 3.01 (d, J = 5.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 166.34, 165.23, 164.40, 152.61, 152.05, 149.98, 149.41, 148.14, 147.50, 143.72, 132.75, 129.90, 127.10, 125.19, 120.90, 120.15, 117.59, 117.12, 115.61, 114.91, 114.15, 110.35, 64.65, 64.21, 26.16.

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; El-Damasy, Ashraf Kareem; Seo, Seon Hee; Cho, Nam-Chul; Kang, Soon Bang; Pae, Ae Nim; Kim, Key-Sun; Keum, Gyochang; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 754 – 768;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of corresponding acids (RCOOH, 0.63 mmol), HOBt (170 mg, 1.26 mmol), EDCI (242 mg, 1.26 mmol), and DIPEA (0.208 mL, 1.26 mmol) were added to DMA (60 mL), and then 4 (186 mg, 1.26mmol) were added, the mixture was stirred overnight. The mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-nitrophenethyl)amide (5) in a good yield. And to a solution of 5 in MeOH was added 10percent Pd/C under H2 at reflux overnight, then the mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-aminophenethyl)amide (6) in a good yield. Then the mixture of 3 and 6 was added NaCNBH3 in MeOH and the solution was stirred under reflux overnight. After reaction completed, the solvent was removed under reduced pressure and the residue was dissolved in water, the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to afford the corresponding compounds (7-26) in good yields.

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
Article; Chen, Wenhua; Yao, Xue; Huang, Zhenghui; Mao, Fei; Guan, Longfei; Tang, Yun; Jiang, Hualiang; Li, Jian; Huang, Jin; Jiang, Lubin; Zhu, Jin; Chinese Chemical Letters; (2019); p. 250 – 254;,
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.

EXAMPLE 120 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester A solution of 19.6 g (109 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (J. Chem. Soc., 3445, 1957) in 400 mL of MeOH containing 4 mL of H2SO4 was refluxed overnight. Sodium bicarbonate (18 g) was added, the solvent was removed and the residue was triturated several times with Et2O. The washes were combined, filtered through anhyd MgSO4 and evaporated to yield 20.7 g of the title compound as a pale yellow oil: mass spectrum (electron impact, m/e): 194.

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

Reference£º
Patent; American Cyanamid Company; US6288082; (2001); B1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem