Acetic Acid → HCID 20070367, compound
Reaction equation
[CH3:1][C:2]([NH:6][C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])([CH3:5])[CH2:3][OH:4].Cl.N.[C:16](O)(=O)[CH3:17]>>[CH3:16][C:17]1[N:6]([C:2]([CH3:1])([CH3:5])[CH2:3][OH:4])[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1Participants
5
Procedure
A mixture of 2-(1,1-dimethyl-2-hydroxyethyl)aminoaniline (from Preparation 2(a)) (8.4 g), acetic acid [4.2 g], and 4N hydrochloric acid [50 ml] were refluxed for 30 hours. The reaction was cooled and neutralised with concentrated aqueous ammonia. The solution was extracted with a mixture of tetrahydrofuran (1 part) and dichloromethane (3 parts) (3×100 ml). The organic phases were combined, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was recrystallised from ethyl acetate yielding the title compound as a white solid 3.8 g (40%), m.p. 180°-181° C.