Hydrochloric Acid → 4-(Bis(2-chloroethyl)amino)benzenepropanoic acid

Reaction equation

Cl.[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:11][CH:10]=1)[CH2:6][CH2:7][Cl:8].[OH-].[Na+]>O>[Cl:2][CH2:3][CH2:4][N:5]([C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[CH2:6][CH2:7][Cl:8]

Participants

Procedure

Concentrated hydrochloric acid (10 ml) was added to 1.5 g (4.93 mmol) of methyl 3-[4-[N,N-bis(2-chloroethyl)amino]phenyl]propionate, followed by stirring under heat for 2.5 hours over an oil bath controlled at 90° C. The reaction mixture was diluted with water and was then adjusted to about pH 2 or so with a 5N aqueous solution of sodium hydroxide. The resultant crystals were collected by filtration, whereby 1.21 g (4.17 mmol) of the title compound were obtained as white crystals (yield: 84.6%).