ChemicalBook CAS DataBase List 1-BENZYL-5-NITRO-1H-INDAZOLE

1-BENZYL-5-NITRO-1H-INDAZOLE synthesis

6synthesis methods

Product Name:1-BENZYL-5-NITRO-1H-INDAZOLE
CAS Number:23856-20-4
Molecular formula:C14H11N3O2
Molecular Weight:253.26

1H-Indazol-3-amine, 5-nitro-1-(phenylmethyl)-

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23856-20-4
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Yield:23856-20-4 90%

Reaction Conditions:

with tert.-butylnitrite in tetrahydrofuran; for 1 h;Reflux;

Steps:

1 General procedure for synthesis of indazole 3

General procedure: A mixture of 3-amino-1-methyl-1H-indazole 2 (3.0 mmol) and tert-butyl nitrite (1.0 mL, 8.1 mmol, 2.7 equiv) in THF (12.0 mL) was heated to reflux for 1 h. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using Et2O/hexanes (1:4) as eluent to give the product 3.

References:

Liu, Han-Jun;Hung, Shiang-Fu;Chen, Chuan-Lin;Lin, Mei-Huey [Tetrahedron,2013,vol. 69,# 19,p. 3907 - 3912]