ChemicalBook CAS DataBase List N-(2-ETHOXY-ETHYL)-BENZENE-1,2-DIAMINE

N-(2-ETHOXY-ETHYL)-BENZENE-1,2-DIAMINE synthesis

5synthesis methods

Product Name:N-(2-ETHOXY-ETHYL)-BENZENE-1,2-DIAMINE
CAS Number:95893-89-3
Molecular formula:C10H16N2O
Molecular Weight:180.25

95893-88-2 Synthesis

95893-88-2
4 suppliers
inquiry

95893-89-3
10 suppliers
inquiry

Yield:95893-89-3 95%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen in ethanol at 5 - 10; under 2250.23 - 3000.3 Torr; for 3 h;

Steps:

3 Example 3: Preparation of N l -(2-ethoxyethyl)benzene- l ,2-diamine 25

N-(2-ethoxyethyl)-2-nitroaniline (20.55 g, 97.74 mmol) was dissolved in ethanol (150 ml) and this solution was cooled under argon to ca. 5- 10°C and 5% Pd-C (1.04 g, 0.5 mol %) was carefully added in portions under stirring. The reaction vessel having been rinsed with nitrogen (3 x 0.203 MPa) the reaction mixture was hydrogenated in a Parr shaking hydrogenator at the hydrogen pressure of 300-400 kPa for 3 h (the reaction was monitored with TLC). After inertization with nitrogen the reaction mixture was filtered through a cellulose filter, the catalyst washed with ethanol (3 x 10 ml) and the filtrate was evaporated until dry in a rotary vacuum evaporator. The crude product (18.07 g, oil of wine colour) was purified by vacuum distillation in a Kugelrohr apparatus (ca. 150-160°C, 4 kPa). The product was obtained as thick yellow oil (16.72 g, 95%), HPLC 99.85%, GC 99.37% and was stored under a nitrogen atmosphere at the temperature of -15°C. -NMR, GC-MS corresponds to the structure

References:

WO2014/26657,2014,A2 Location in patent:Page/Page column 14