4073-98-7

Off-white powder

Notclassified

To a mixed solution of 2,6-dimethylaniline (10.00 g, 0.083 mol) and formaldehyde (4.03 g, 0.054 mol, 0.65 equiv) was slowly added dilute hydrochloric acid (2.2 ml, 0.1 M). The reaction mixture was stirred at 70 °C overnight. After completion of the reaction, the dark red solution was cooled to room temperature and diluted with dichloromethane (15 ml). Subsequently, a minimum amount of concentrated hydrochloric acid (2 ml) was added dropwise to the solution and stirring was continued for 2 h at room temperature followed by filtration. The resulting white salt was washed well with dichloromethane and dried in air. The dried salt was suspended in ether (70 ml), saturated aqueous sodium hydroxide solution was added and stirred until the solid was completely dissolved. The aqueous phase was extracted with ether (2 x 70 ml), the organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product 4-(4-amino-3,5-dimethylbenzyl)-2,6-dimethylaniline (2a) as an orange solid (8.97 g, 86% yield).

[1] Russian Journal of Organic Chemistry, 2009, vol. 45, # 4, p. 528 - 535
[2] Patent: WO2005/118605, 2005, A1. Location in patent: Page/Page column 107
[3] Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 5, p. 319 - 326
[4] Monatshefte fuer Chemie, 1898, vol. 19, p. 641
[5] Journal of Materials Chemistry, 1999, vol. 9, # 7, p. 1425 - 1429