Method of producing methoxyimino acetic amide

A process for preparing a compound of the Formula (I),

• in which
• R1, R2, R3 and R4 are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl,
• R5 represents substituted or unsubstituted alkyl,
• R6 represents hydrogen, substituted or unsubstituted alkyl, selected from the group of processes A, B, C and D,defined below wherein said process A comprises in a process step (2), the step of reacting in the presence of an acid or an acidic ion exchanger a compound of the Formula (IV),
• in which
• R1, R2, R3 and R4 are as defined above,
• with
• an alcohol of the Formula (V),
• R7—OH (V)
• in which
• R7 represents substituted or unsubstituted alkyl, and with a carbonyl compound, which binds hydroxylammonium chloride eliminated in the reaction forming an oxime, to give a compound of the Formula (VI),
• in which
• R1, R2, R3, R4 and R7 are as defined above,
• and the resulting compound of the Formula (VI) is either
• a) according to a process step (3), reacted with a hydroxylammonium salt, optionally in the presence of a diluent and optionally in the presence of an acid or an acid acceptor, to give a compound of the Formula (VII),
• in which
• R1, R2, R3, R4 and R7 are as defined above,
• and the resulting compound of the Formula (VII) is, according to a process step (4), reacted with an alkylating agent of the Formula (VIII),
• R5—X (VIII)
• in which
• R5 is as defined above and
• X represents halogen or —O—SO2—O—R5, where R5 is as defined above, optionally in the presence of a diluent and optionally in the presence of a base, or
• b) according to a process step (5), reacted with an alkoxyamine of the Formula (IX),
• R5—O—NH2 (IX)
• in which
• R5 is as defined above,
• or an acid addition complex thereof, optionally in the presence of a diluent and optionally in the presence of an acid or an acid acceptor, and,
• wherein said process B comprises in a process step (6), the step of reacting a compound of the Formula (IV),
• in which
• R1, R2, R3 and R4 are as defined above, with an alkoxyamine of the Formula (IX),
• R5—O—NH2 (IX)
• in which
• R5 is as defined above,
• or an acid addition complex thereof optionally in the presence of a diluent and optionally in the presence of an acid, and
• wherein said process C comprises in a process step (7), the step of reacting in the presence of an acid or an acidic ion exchanger a compound of Formula (IV),
• in which
• R1, R2, R3 and R4 are as defined above, with
• an alcohol of the Formula (V),
• R7—OH (V)
• in which R7 is as defined above,
• optionally with addition of a hydroxylammonium salt, and the resulting compound of the Formula (VII),
• in which
• R1, R2, R3, R4 and R7 are as defined above,
• is reacted according to said process step (4), and
• wherein said process D comprises in a process step (8), the step of reacting in the presence of an acid or an acidic ion exchanger a compound of the Formula (X),
• in which
• R1, R2, R3, R4 and R5 are as defined above, with an alcohol of the Formula (V),
• R7—OH (V)
• in which R7 is as defined above,
• optionally in the presence of a carbonyl compound which binds hydroxylammonium chloride eliminated in the reaction forming an oxime, and
• wherein the compound of the Formula (II) obtained according to any of said processes A through D,
• in which
• R1, R2, R3, R4 and R5 are as defined above and
• R7 represents unsubstituted or substituted alkyl, is, optionally reacted according to a process step (1) without intermediate isolation of the compound of the Formula (II) from a reaction vessel (one-pot process), with an alkylamine of the Formula (III),
• R6—NH2 (III)
• in which
• R6 is as defined above, optionally in the presence of a diluent.