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ChemicalBook CAS DataBase List 1H-Indazol-5-ol, 4-chloro-
478834-25-2

1H-Indazol-5-ol, 4-chloro- synthesis

3synthesis methods
1H-Indazol-5-ol

15579-15-4

1H-Indazol-5-ol,  4-chloro-

478834-25-2

At room temperature, 1H-indazol-5-ol (1.60 g, 11.9 mmol) was dissolved in tetrahydrofuran (50 mL) and N-chlorosuccinimide (1.59 g, 11.9 mmol) was added. After 1 hour of reaction, the mixture was warmed up to 40 °C to continue the reaction for 2 hours, followed by warming up to 50 °C for 5 hours. Upon completion of the reaction, the reaction solution was poured into water (100 mL) and extracted with ethyl acetate (3 × 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-chloro-5-hydroxy-1H-indazole (1.7365 g, 86% yield).1H-NMR (DMSO-d6) δ: 7.09 (1H, d, J = 8.8 Hz), 7.33 (1H, d, J = 8.8 Hz), 7.90 (1H, s) 9.71 (1H, s), 13.10 (1H, s).

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Yield:478834-25-2 86%

Reaction Conditions:

with N-chloro-succinimide in tetrahydrofuran at 20 - 50; for 8 h;

Steps:

468 Example 468; Synthesis of 4-chloro-1H-indazol-5-ol

To a solution of the 1H-indazol-5-ol (1.60 g, 0.0119 mol) obtained in Reference Example 4 in tetrahydrofuran (50 ml) was added N-chlorosuccinimide (1.59 g, 0.0119 mol) at room temperature. After 1 hour, the mixture thus obtained was heated to 40°C, and after another 2 hour, the mixture was heated to 50°C. After 5 hours, the reaction solution was poured into water (100 ml) and extracted with ethyl acetate (100 ml x 3). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-chloro-1H-indazol-5-ol (1.7365 g, 86%).1H-NMR (DMSO-d6) δ; 7.09 (1H, d, J=8.8Hz), 7.33 (1H, d, J=8.8Hz), 7.90 (1H, s), 9.71 (1H, s), 13.10 (1H, s).

References:

EP1403255,2004,A1 Location in patent:Page 120

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