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ChemicalBook CAS DataBase List 3-HYDROXY-4,6-DIFLUORO-(1H)INDAZOLE
887567-77-3

3-HYDROXY-4,6-DIFLUORO-(1H)INDAZOLE synthesis

2synthesis methods
79538-28-6 Synthesis
Methyl 2,4,6-trifluorobenzoate

79538-28-6
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$13.00/250mg

3-HYDROXY-4,6-DIFLUORO-(1H)INDAZOLE

887567-77-3
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Yield:887567-77-3 76%

Reaction Conditions:

with hydrazine hydrate in tetrahydrofuran;ethanol at 70; for 24 h;

Steps:

4.2.4. 3-Hydroxy-4,6-difluoro-1H-indazole (20)

In a three-neck round-bottom flask equipped with a reflux condenser, methyl 2,4,6-trifluorobenzoate (49) (0.20 g, 1.1 mmol) was dissolved in tetrahydrofuran (20 mL); then, a solution of 98% hydrazine monohydrate (0.15 g, 3.0 mmol) in ethanol (10 mL) was added dropwise. The mixture was heated at 70 °C for 24 h. After cooling at room temperature, the solution was decanted and the organic solvent evaporated under vacuum. The solid residue was washed with dichloromethane and dried to afford 20 (0.13 g, 76%) as a white solid. Mp 293.5 °C. Anal. Calcd for C7H4F2N2O: C, 49.42; H, 2.37; N, 16.47. Found: C, 49.44; H, 2.49; N, 16.27. 1H NMR (DMSO-d6) δ 11.8 (br s, 1H, NH), 10.9 (br s, 1H, OH), 6.71 (ddd, 3JF4 = 3JF6 = 10.3, 4JH7 = 1.9, 1H, H5), 7.09 (dd, 3JF6 = 9.2, 4JH5 = 1.9, 1H, H7); 19F NMR (DMSO-d6) δ -115.9 (dd, 3JH5 = 9.6, 4JF6 = 8.4, F4), -111.6 (br s, F6); 13C NMR (DMSO-d6) δ 153.6 (s, C3), 98.9 (d, 2J = 20.2, C3a), 155.7 (dd, 1J = 253.3, 3J = 16.7, C4), 94.4 (dd, 2J = 30.5, 2J = 23.3, C5), 161.8 (dd, 1J = 242.7, 3J = 11.7, C6), 92.0 (dd, 2J = 26.1, 4J = 4.7, C7), 143.6 (dd, 3J = 15.1, 3J = 10.3, C7a); 15N NMR (THF-d8, T = 207 K) δ -224.1 (N1, 1J = 107.1), -117.9 (N2).

References:

Claramunt, Rosa M.;López, Concepción;López, Ana;Pérez-Medina, Carlos;Pérez-Torralba, Marta;Alkorta, Ibon;Elguero, José;Escames, Germaine;Acu?a-Castroviejo, Darío [European Journal of Medicinal Chemistry,2011,vol. 46,# 4,p. 1439 - 1447] Location in patent:experimental part

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