Water → 2-(Methyl(4-nitrophenyl)amino)ethan-1-ol

Participants

Reaction Steps

5.25 g of N-methylethanolamine, 11.2 g of p-nitrofluorobenzene, 9.7 g of K2CO3 and 2 drops of tricaprylmethylammonium chloride in 70 ml of dimethylformamide were heated at 95° C. for 3 days. The resulting reaction mixture was poured onto 350 ml of water. The precipitated product was filtered off under suction, after which the aqueous phase was extracted with toluene. After drying and evaporating down the toluene solution, the two product fractions were combined and recrystallized from ethanol/water in a volume ratio of 2 1. 10.22 g of 2-[N-(p-nitrophenyl)-N-methylamino]-ethanol having the following physical properties were obtained: melting point: 99°-101° C., IR spectrum (KBr pellet): bands at 3,450, 2,900, 2,850, 1,690, 1,680, 2,900, 1,580, 1,470, 1,450, 1,330, 1,320, 1,110, 1,060 and 825 cm-1 ; 1H nuclear magnetic resonance spectrum (400 MHz, CDCl3, tetramethylsilane as internal standard, chemical shift δ (in ppm): 8.05 (doublet, 2H), 6.64 (doublet, 2H), 3.9 (triplet, 2H), 3.65 (triplet, 2H), 3.15 (singlet, 3H) 2.02 (singlet, 1H).

Provenance & Evidence