Dichloromethane → N-(2-aminoethyl)-3-bromopyridine-2-carboxamide hydrochloride
Reaction equation
[Br:1][C:2]1[C:3]([C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:29]>>[ClH:29].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([C:3]1[C:2]([Br:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:9]Participants
4
Procedure
3.2 g of t-butyl [2-(3-bromopyridine-2-carboxamido)ethyl]carbamate were heated to reflux for 4 hours with 3.5 ml of methylene chloride and 3.5 ml of trifluoroacetic acid. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethanol and the solution was treated with an equimolar amount of ethanolic hydrochloric acid. The hydrochloride was recrystallized from methanol/ether, whereby there was obtained N-(2-aminoethyl)-3-bromopyridine-2-carboxamide hydrochloride as white crystals, m.p. 279°.