Efficient Synthesis of N,N-Disubstituted 5-Aminothiophene-2-carboxaldehydes by Nucleophilic Aromatic Substitution in Water

We have developed the first synthesis of N,N-disubstituted 5-aminothiophene-2-carboxaldehydes by nucleophilic aromatic substitution of 5-bromothiophene-2-carboxaldehyde in water. This study shows selectivity between primary and secondary amines leading to the corresponding imines or amino derivatives respectively.