ChemicalBook CAS DataBase List 5-Nitroindazole

5-Nitroindazole synthesis

7synthesis methods

Product Name:5-Nitroindazole
CAS Number:5401-94-5
Molecular formula:C7H5N3O2
Molecular Weight:163.13

27996-87-8

5401-94-5

General procedure: hydrazine hydrate (NH2NH2-H2O, 3.0 mmol) was added dropwise to a stirred solution of 2-fluoro-5-nitrobenzaldehyde (1.0 mmol) in DMF (5 mL) at 23 °C. The reaction mixture was stirred continuously at the same temperature for 2 h. The progress of the reaction was monitored by thin-layer chromatography (TLC, unfolding agent: 20% ethyl acetate in hexane solution) to confirm the complete conversion of the starting material 2-fluoro-5-nitrobenzaldehyde. Upon completion of the reaction, the crude reaction mixture was poured into water and extracted with ethyl acetate (2 x 15 mL). The organic phases were combined, washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give pure 5-nitroindazole.

99-52-5 Synthesis

99-52-5
288 suppliers
$5.00/5 g

5401-94-5
377 suppliers
$14.00/5g

Yield:5401-94-5 100%

Reaction Conditions:

with acetic acid;sodium nitrite in water at 0 - 20; for 72 h;

Steps:

Synthesis of 3-chloro-lH-indazol-5-amine (10):
To a solution of 2-m ethyl -4-nitroaniline (298 mg, 1.96 mmol), in acetic acid maintained at 0 °C was added dropwise sodium nitrite (135.2 mg, 1.96 mmol) dissolved in water. The reaction was stirred at room temperature for 72 h. The reaction mixture was concentrated on rotary evaporator and the residue was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 5-nitro-lH-indazole (6) in quantitative yield.

References:

RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY;FREUNDLICH, Joel S.;ALLAND, David;NEIDITCH, Matthew B.;KUMAR, Pradeep;CAPODAGLI, Glenn;AWASTHI, Divya;EKINS, Sean WO2019/46467, 2019, A1 Location in patent:Page/Page column 37-38

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27996-87-8 Synthesis

27996-87-8
179 suppliers
$5.00/1g

5401-94-5
377 suppliers
$14.00/5g

References