ChemicalBook CAS DataBase List 2-Amino-5-nitrobenzophenone

2-Amino-5-nitrobenzophenone synthesis

11synthesis methods

Product Name:2-Amino-5-nitrobenzophenone
CAS Number:1775-95-7
Molecular formula:C13H10N2O3
Molecular Weight:242.23

17420-30-3

873-55-2

1775-95-7

2-Cyano-4-nitroaniline (0.3 mmol), sodium benzenesulfinate (0.6 mmol), palladium acetate (10 mol%), 2,2'-bipyridine (20 mol%), p-nitrobenzenesulfonic acid (10 equiv.), tetrahydrofuran (2 mL), and water (1 mL) were sequentially added to a Schlenk tube under the protection of nitrogen atmosphere. The reaction mixture was stirred vigorously at 80 °C for 48 hours. After completion of the reaction, the mixture was poured into ethyl acetate and washed sequentially with saturated sodium bicarbonate solution (2 x 10 mL) and saturated saline (1 x 10 mL). After the aqueous layer was extracted with ethyl acetate, all organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by fast column chromatography (eluent: hexane/ethyl acetate) to afford the target product 2-amino-5-nitrobenzophenone.

17420-30-3 Synthesis

17420-30-3
315 suppliers
$7.00/25g

873-55-2 Synthesis

873-55-2
408 suppliers
$10.00/5g

1775-95-7
292 suppliers
$10.00/5g

Yield:1775-95-7 96%

Reaction Conditions:

with p-nitrobenzenesulfonic acid;palladium diacetate in tetrahydrofuran;water at 80; for 48 h;Inert atmosphere;Schlenk technique;

Steps:

General Procedure for the Synthesis of o-Aminobenzophenones
General procedure: Under a N₂ atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)₂ (10 mol %), bpy (20 mol %), p-NBSA (10 equiv), THF (2 mL), and H₂O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO₃ (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO₄ and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3.

References:

Chen, Jiuxi;Li, Jianjun;Su, Weike [Molecules,2014,vol. 19,# 5,p. 6439 - 6449]

FullText