2-(2-Hydroxyethyl)-p-phenylenediamine synthesis

4synthesis methods

Product Name:2-(2-Hydroxyethyl)-p-phenylenediamine
CAS Number:19298-14-7
Molecular formula:C8H12N2O
Molecular Weight:152.19

N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenylene-1,4-diamine

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Yield:19298-14-7 97%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol at 20; under 760.051 Torr;Inert atmosphere;

Steps:

12A

Example 12A2-[(4-Aminophenyl)amino]ethanol Under argon, 200 mg of palladium on activated carbon (10%) are added to a solution of 2.0 g (11 mmol) of 2-[(4-nitrophenyl)amino]ethanol (Example 11A, Step a)) in 30 ml of ethanol, and the mixture is hydrogenated at RT and atmospheric pressure under an atmosphere of hydrogen. The catalyst is removed via a filter bed and washed with ethanol, and the filtrate is concentrated under reduced pressure.Yield: 1.7 g (97% of theory)LC-MS (method 5): R_t=0.47 min;MS (ESIpos): m/z=153 [M+H]⁺;¹H-NMR (300 MHz, DMSO-d₆): δ=6.45-6.31 (m, 4H), 4.59 (t, 1H), 4.50 (br. s, 1H), 4.21 (br. s, 2H), 3.52 (q, 2H), 2.97 (t, 2H).

References:

US2010/10060,2010,A1 Location in patent:Page/Page column 21