ChemicalBook CAS DataBase List 3'-Aminobenzanilide

3'-Aminobenzanilide synthesis

12synthesis methods

Product Name:3'-Aminobenzanilide
CAS Number:16091-26-2
Molecular formula:C13H12N2O
Molecular Weight:212.25

55-21-0 Synthesis

55-21-0
388 suppliers
$5.00/5 g

591-19-5
318 suppliers
$10.00/10g

16091-26-2
122 suppliers
$20.00/1 g

Yield: 92%

Reaction Conditions:

with copper(l) iodide;dimethylaminoacetic acid;potassium carbonate in N,N-dimethyl-formamide at 100; for 24 h;Schlenk technique;Inert atmosphere;Goldberg Reaction;

Steps:

3.3. General Procedure for the Coupling of Aryl Bromides with Amides Using Copper/N,N-DimethylglycineCatalytic System
General procedure: A Schlenk tube was charged with amide (1.2 mmol), aryl halide (1 mmol), CuI (0.05 or 0.1 mmol), N,N-dimethylglycine (0.1 or 0.2 mmol), and potassium carbonate (2 mmol). The tube was evacuated and backfilled with argon at room temperature. DMF (0.5 mL) was added under argon via syringe. The Schlenk tube was immersed in a preheated oil bath and the reaction mixture was stirred for the specified time at the indicated temperature. The cooled mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate.The combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:8 to 1:2 ethyl acetate/petroleum ether) to give the the desired N-aryl amides.

References:

Jiang, Liqin [Molecules,2014,vol. 19,# 9,p. 13448 - 13460] Location in patent:supporting information