Réaction #502119

Équation de réaction

Ethyl(2-(hydroxy)ethyl)amine

HNO3

→

title compound

Rendement 76.1%

Ethyl(2-(nitrooxy)ethyl)ammonium nitrate

Rendement 76.1%

Solvants

EtOAc

EtOAc

hexane

Conditions de réaction

Traitement

1. 1
   AutreThe oil layer was separated
2. 2
   Autredried in high vacuo

Mode opératoire

Ethyl(2-(hydroxy)ethyl)amine (5 g, 56 mmol) in EtOAc (60 mL) was added drop-wise to a mixture of fuming HNO3 (17.7 g, 11.8 mL, 280 mmol) and Ac20 (45.8 g, 42.3 mL, 448 mmol) at −10° C. The reaction mixture was stirred at −10° C. for 30 minutes and diluted with EtOAc and hexane. The oil layer was separated and dried in high vacuo to give the title compound (8.4 g, 76% yield) as a pale green oil. 1H NMR (300 MHz, d6-DMSO) δ 8.60-8.95 (bs, 2H), 4.84 (m, 2H), 3.37-3.49 (m, 2H), 3.02-3.16 (m, 2H), 1.24 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) δ 69.1, 43.6, 42.6, 11.0. Mass spectrum (API-TIS) m/z 135 (MH+).

Source