2-Acetyl-5-iodothiophene → 2-Acetyl-5-(aminomethyl)thiophene

Participants

Reaction Steps

Starting with the readily available compound, denoted 2, 5-iodo-2-acetylthiophene ##STR2## and using a procedure described by S. Nishimura and E. Imoto, Nippon Kagaku Zasshi 82, 1411 (1961), incorporated by reference herein, one generates 5-cyano-2-acetylthiophene denoted 3 below, ##STR3## The "blocked" form is then generated according to standard methods. See for example W. S. Johnson et al., J. Amer. Chem. Soc. 78, 6300, (1956), incorporated by reference herein. This results in a compound, denoted 4 below, ##STR4## Compound 4 is then reduced with available methods such as the one described by R. F. Nystrom and W. G. Brown, J. Amer. Chem. Soc. 70, 3738 (1948), incorporated by reference herein, and then "deblocked" (see for example W. S. Johnson et al. above) to give 2-acetyl-5-(aminomethyl)thiophene, 5,: ##STR5## Then using standard Claisen condensation techniques, such as described by J. C. Reid and M. Calvin, J. Amer. Chem. Soc. 72, 2948 (1950), incorporated by reference herein, the chelating ligand 1 is synthesized, abbreviated hereafter as TTFA-NH2.

Provenance & Evidence