Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-02-19
1999-08-24
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546288, 546292, 546296, 546297, 546298, 562465, 562496, C07D21355, C07D21357, C07D21363, C07D21378
Patent
active
059426233
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a chemical process and, more particularly, to a process for preparing 2-(pyrid-2-yloxymethyl)phenylacetates. These compounds are useful as intermediates for producing agricultural pesticides.
Some new agricultural fungicides and insecticides, which are methyl described in EP-A 0278595 along with a variety of methods for their preparation. In one method described, 3-isochromanone is converted into a methyl 2-halomethylphenylacetate using a hydrogen halide in methanol, followed by reaction with the metal salt of a hydroxyaryl or heteroaryl compound and the subsequent transformation of the methyl acetate group into a methyl methoxyacrylate group. The transformation is said also to be accomplished in two steps if the isochromanone is treated with the hydrogen halide in a non-alcoholic solvent and the resulting phenylacetic acid esterified. In another method, when the aryl or heteroaryl group is sufficiently activated, the compounds may be prepared from a methyl 2-(2-hydroxymethylphenyl)-3-methoxyacrylate and an aryl or heteroaryl species containing a leaving group such as a halide group or a CH.sub.3 SO.sub.4 anion or sulphonyloxy anion, often in the presence of a base such as sodium hydride, potassium t-butoxide or potassium carbonate.
The present invention provides a novel process for preparing methyl 2-(pyrid-2-yloxy-methyl)phenylacetate intermediates for use in the pesticides.
According to the present invention there is provided a process for preparing a methyl 2-pyrid-2-yloxymethyl)phenylacetate of formula (I).sup.1 wherein A and D are independently H, halo, haloalkyl, haloalkoxy, phenyl, phenoxy, nitro, amino, acylamino, cyano, carboxy, alkoxycarbonyl or alkylcarbonyloxy or equivalent and m is 0 or an integer of from 1 to 3 provided that A is other than H when m is an integer of from 1 to 3, which comprises reacting a 2-pyridine of formula (II) wherein L is a leaving group and A, D and m are as defined above, with a compound MO--CH.sub.2 R wherein M is a metal atom and R is the residue of a metal salt of 2-phenylacetic acid, and methylating the metal salt of the 2-pyridyloxymethyl-phenylacetic acid so obtained. chemical structures.
Halo is typically fluorine, chlorine or bromine.
The alkyl moiety of haloalkyl, haloalkoxy, alkoxycarbonyl and alkylcarbonyloxy contains for example, from 1 to 8 or 1 to 6, typically from 1 to 4, carbon atoms in the form of straight or branched chains. Examples are methyl, ethyl, n- and iso-propyl, n-, sec, iso- and tert-butyl, n-hexyl and n-octyl.
Examples of haloalkyl groups include halo(C.sub.1-4)alkyl, typically halomethyl and haloethyl, which include trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl and pentafluoroethyl. Examples of haloalkoxy are trifluoro-and trichloromethoxy. Examples of alkoxycarbonyl and alkylcarbonyloxy are methoxycarbonyl and acetoxy. Acylamino includes, in particular, C.sub.1-4 alkenylamino, for example, formamido and acetylamino.
Phenyl and phenoxy groups may themselves be substituted by one or more substituents. Suitable substituents include, for example, halo, C.sub.1-4 alkyl, halo(C.sub.1-4)alkyl, C.sub.1-6 alkoxy, thio(C.sub.1-4)alkoxy, halo(C.sub.1-4)alkoxy, phenyl, phenoxy, cyano, nitro, amino, mono- or di-(C.sub.1-4)alkylamino, C.sub.1-4 alkanoylamino, carboxy, C.sub.1-4 alkoxycarbonyl or C.sub.1-4 alkylcarbonyloxy.
Where m is 2 or 3, the substituent D may have the same or different values.
The metal atom M in the compound MO--CH.sub.2 R and the metal in the metal salt of the residue R may be an alkali or alkaline earth metal, or it could be another metal, for example, silver. Usually, it will be sodium or potassium and M and the metal in the metal salt of the residue R will be the same. Thus the compound MO--CH.sub.2 R will usually be the di-sodium or di-potassium salt of 2-hydroxymethylphenylacetic acid.
The leaving group L of the pyridine of formula (II) is in the 2-position of the pyridine ring and is any suitable leaving group for ether formation with a benzyl
REFERENCES:
patent: 4045438 (1977-08-01), Haviv et al.
patent: 4128572 (1978-12-01), Cassar et al.
Chemical Abstracts, vol. 121, 83940, 1994.
Chemical Abstracts, vol. 117, 192087, 1992.
Chemical Abstracts, vol. 115, 136720, 1991.
Chemical Abstracts, vol. 112, 235795, 1990.
Chemical Abstracts, vol. 99, 175202, 1983.
Chemical Abstracts, vol. 92, 147010, 1980.
Chemical Abstracts, vol. 88, 6363, 1978.
Abstract of Jiansheng Wang M.S. Dissertation, E. Michigan Univ., 1989.
Munns Gordon Richard
Williams Alfred Glyn
Worthington Paul Anthony
LeCroy David P.
Rotman Alan L.
Zeneca Limited
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