Process for the preparation of 4-haloalkylnicotinonitriles

Details Process for the preparation of 4-haloalkylnicotinonitriles Process for the preparation of 4-haloalkylnicotinonitriles

2005-03-08

2005-03-08

McKane, Joseph K. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

C558S441000, C558S436000

Reexamination Certificate

active

06864385

ABSTRACT:
4-Haloalkylnicotinonitriles having the formula (I)which are suitable as intermediates in the preparation of pesticides, are obtained by:(a) reacting a 3-amino-1-haloalkyl-2-propen-1-onein-line-formulae description="In-line Formulae" end="lead"?RF—C(O)—CH═CH—NH2  (II)in-line-formulae description="In-line Formulae" end="tail"?in a condensation reaction with a compound of the formula (III) to (VII),in-line-formulae description="In-line Formulae" end="lead"?(R1Z)CH═CH—CN  (III)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?(R1Z)2CH—CH2—CN  (IV)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Hal-CH═CH—CN  (V)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?Hal2CH—CH2CN  (VI)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?HC≡C—CN  (VII),in-line-formulae description="In-line Formulae" end="tail"?to give a compound of the formula (VIII), (IX) and/or (X),in-line-formulae description="In-line Formulae" end="lead"?RF—C(O)—CH═CH—NH—CH═CH—CN  (VIII)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?RF—C(O)—CH═CH—NH—CH(ZR1)—CH2—CN  (IX)in-line-formulae description="In-line Formulae" end="tail"?in-line-formulae description="In-line Formulae" end="lead"?RF—C(O)—CH═CH—NH—CH(Hal)—CH2—CN  (X),in-line-formulae description="In-line Formulae" end="tail"?wherein RFis (C1-C4)-haloalkyl, R1is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR1or OCO; and(b) subjecting the reaction product to a ring closure reaction.

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