Reaction #502110

Reaction equation

4-fluoronitrobenzene

diethanolamine

→

title compound

Yield 85.0%

2-((Hydroxyethyl)(4-nitrophenyl)amino)ethan-1-ol

Yield 85.0%

Solvents

methanol dichloromethane

Conditions

Procedure

A mixture of 4-fluoronitrobenzene (5 g, 35 mmol) and diethanolamine (7.5 g, 71 mmol) was heated to 130° C. without solvent for 4 hours. The crude reaction mixture after chromatography on silica gel (gravity, methanol: dichloromethane 1:19 then 1:9) gave the title compound (6.7 g, 85% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.98 (d, 2H), 6.78 (d, 2H), 4.83 (t, 2H), 3.50-3.65 (m, 8H). 13C NMR (75 MHz, DMSO-d6) 6 154.36, 136.16, 126.77, 111.66, 58.89, 54.17. Mass spectrum m/z 227 (MH+). Anal. calcd. for C10H14N2O4 C, 53.09; H, 6.24; N, 12.38. Found C, 53.09, H, 6.32, N, 12.34.

Source