Process for the preparation of 4-haloalkylnicotinonitriles

A process for the preparation of a compound having the formula

• wherein RF is (C1-C4)-haloalkyl, said process comprising:
• (a) reacting a 3-amino-1-haloalkyl-2-propen-1-one having the formula (II):
• RF—C(O)—CH═CH—NH2 (II)
• wherein RF is defined as above, in a condensation reaction with at least one compound having a formula selected from the group consisting of (III), (IV), (V), (VI) and (VII):
• (R1Z)CH═CH—CN (III)
• (R1Z)2CH—CH2—CN (IV)
• Hal-CH═CH—CN (V)
• Hal2CH—CH2CN (VI)
• HC≡C—CN (VII)
• wherein R1 is alkyl, Hal is Cl or Br and each Z is, independently, O, S, NR1 or OCO;
• to afford at least one compound having a formula selected from the group consisting of (VIII), (IX) and (X):
• RF—C(O)—CH═CH—NH—CH═CH—CN (VIII)
• RF—C(O)—CH═CH—NH—CH(ZR1)—CH2—CN (IX)
• RF—C(O)—CH═CH—NH—CH(Hal)—CH2—CN (X)
• wherein RF, R1, Z and Hal are as defined above;
• (b) subjecting the reaction product of step (a) to a ring closure reaction to afford the corresponding compound having the formula (I):
• wherein RF is defined as above;
• and
• (c) hydrolyzing the resultant compound having the formula (I), to afford the corresponding compound having the formula (XI).