Process for preparing 3-aminophenylacetylenes

A process for preparing a 3-aminophenylacetylene compound represented by formula (5), comprising:

• a) reacting a 3-haloaniline compound represented by formula (1) with an acetylene compound represented by formula (2) in the presence of a palladium compound, a copper compound, and an amine compound represented by formula (3) to form an aniline compound represented by formula (4);
• b) precipitating the resultant aniline compound represented by formula (4) in the form of a crystal, and isolating it by solid/liquid separation;
• and
• c) reacting the aniline compound represented by formula (4) obtained in the above b) with a base to obtain 3-aminophenylacetylene represented by formula (5):
• wherein, in formulae (1) to (4), Y represents a halogen atom;
• R1 and R2 each independently represent a hydrogen atom, a sustituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or R1 and R2 may combine with each other to form a ring;
• R3 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms;
• and R4 and R5 each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or R4 and R5 may combine with each other to form a ring.