Ethanolamine → HC Yellow no. 12

Participants

Reaction Steps

A mixture of 1,4-dichloro-2-nitrobenzene (I-1, Aldrich, Wis.; 38.4 g, 0.2 mol) and 2-aminoethanol (24.4 g, 0.4 mol, 2 eq.) in n-butanol (100 mL) was refluxed overnight. The solvent was evaporated and the residue was dispersed in petrol ether (600 mL) and stirred overnight. The solids were filtered to give intermediate I-2 as a yellow powder (37 g, 86%). 1H-NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 8.19˜8.20 (d, 1H, J=2.4 Hz), 7.39˜7.42 (dd, 1H, J1=2.4 Hz, J2=9.2 Hz), 6.87˜6.90 (d, 1H, J=9.6 Hz), 3.95˜3.98 (t, 2H, J=5.2 Hz), 3.49˜3.53 (dd, 2H, J1=4.8 Hz, J2=10.4 Hz). MS (ESI): m/z 217 (M+H+).

Provenance & Evidence