Process for the preparation of 4-haloalkylnicotinonitriles

US6541640B2 · kind B2 · utility

Assignee

• Aventis CropScience GmbH · DE

Inventors

• Sergiy Pazenok · Kelkheim, DE
• Henricus Maria Martinus Bastiaans · Raleigh, US

Key dates

• Filing date: Dec 13, 2001
• Grant date: Apr 1, 2003
• Expiry date: Dec 13, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D213/85
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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-oneRF—C(O)—CH═CH—NH2  (II) in a condensation reaction with a compound of the formula (III) to (VII),(R1Z)CH═CH—CN  (III)(R1Z)2CH—CH2—CN  (IV)Hal-CH═CH—CN  (V)Hal2CH—CH2CN  (VI)HC≡C—CN  (VII), to give a compound of the formula (VIII), (IX) and/or (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 is (C1-C4)-haloalkyl, R1 is alkyl, Hal is Cl or Br and each Z, independently, is O, S, NR or OCO; and(b) subjecting the reaction product to a ring closure reaction.