PROCESS FOR PREPARING KETONES OR ALDEHYDES

Title:

PROCESS FOR PREPARING KETONES OR ALDEHYDES

Document Type and Number:

WIPO Patent Application WO/2000/069800

Kind Code:

A2

Abstract:

The invention relates to a process for preparing compounds of formula (I), wherein R?1¿ and R?2¿ are as defined in the description.

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Inventors:

GRIENEISEN JEAN-LOUIS (FR)
JACQUOT ROLAND (FR)

Application Number:

PCT/EP2000/004594

Publication Date:

November 23, 2000

Filing Date:

May 11, 2000

Export Citation:

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Assignee:

AVENTIS CROPSCIENCE SA (FR)
GRIENEISEN JEAN LOUIS (FR)
JACQUOT ROLAND (FR)

International Classes:

C07C45/27; C07C45/32; C07C201/12; C07C205/11; C07C205/45; C07C319/14; C07D261/08; C07C323/22; (IPC1-7): C07C45/00

Domestic Patent References:

WO1998055446A1	1998-12-10
WO1998055437A1	1998-12-10
WO1997028122A2	1997-08-07

Foreign References:

DE859009C	1952-12-11
EP0527036A1	1993-02-10

Other References:

J G REID ET AL: "Addition of nitroalkanes to ortho-halo-nitrobenzenes. A new synthesis of 4-chloro-7-(trifluoromethyl)quinoline" TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 8, no. 31, 1990, pages 1093-1096, XP002074108 ISSN: 0040-4039 cited in the application

Attorney, Agent or Firm:

AVENTIS CROPSCIENCE S.A. (Département Propriété Industrielle Boîte postale 9163 Lyon Cedex 09, FR)
Tetaz, Franck M. (AVENTIS CropScience SA BP 9163 LYON CEDEX 09, FR)

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Claims:

CLAIMS

1.

A process for the preparation of a compound of formula (I): wherein RI and R2, which may be the same or different, each represent hydrogen, unsubstituted or substituted C 1C6 alkyl, unsubstituted or substituted C3C7 cycloalkyl, unsubstituted or substituted 57 membered ring aryl, or unsubstituted or substituted 57 membered ring heteroaryl which contains one to four hetero atoms selected from O, N and S; or RI and R2 together with the carbon atom to which they are attached represent unsubstituted or substituted C3C7 cycloalkyl; which process comprises the direct oxidation of a nitro compound of formula (II) : wherein Rl and R2 are as defined above.

2.	A process according to claim 1 wherein the reaction is performed in an aprotic solvent in the presence of air.

3.	A process according to claim 1 or 2 in which the solvent is selected from dimethylsulphoxide, N, Ndimethylformamide, Nmethylpyrrolidone and sulpholane.

4.

A process according to claim 1,2 or 3 in which a compound of formula (III): wherein: R6 is halogen, R3, C1C6 alkoxy, C1C6 haloalkoxy,S (O) mR3, cycloalkyl having from 3 to 7 ring carbon atoms, C2C6 alkenyl or C2 C6 alkynyl, or (CR4R5) qS (O) pR3 wherein p is 0,1 or 2 and q is 1 or 2; R3 is C 1C6 alkyl or C 1C6 haloalkyl; and R4 and R5 independently represent hydrogen, C 1C6 alkyl or C 1C6 haloalkyl; and n is zero or an integer from one to three; is prepared from a nitro compound of formula (IV): wherein R6 and n are as defined above.

5.	A process according to claim 4 in which the compound of formula (IV) is prepared by the reaction of a compound of formula(V): wherein R6 and n are as defined in claim 4, and X represents halogen preferably chlorine or fluorine; with nitroethane and a base.

6.	A process according to claim 4 or 5, in which further comprises the reaction of a compound of formula (III) with a compound of formula (VI): R7SH (VI) wherein R7 represents C 1C6 alkyl, to prepare a compound of formula (VII): wherein R6 and n are as defined in claim 4.

7.	A process according to any one of claims 2 to 6 in which theNO2 group in the phenyl ring of formula (IV) is located at the 2position relative to the nitroethyl group.

8.	A process according to any one of claims 2 to 7 in which R6 represents trifluoromethyl.

9.	A process according to any one of claims 28 in which R7 represents methyl.

10.	A process according to any one of the preceding claims which further comprises converting a compound of formula (I) into a pesticidal 4benzoylisoxazole compound.

Description:

INTERNATIONALSEARCH REPORT | Inte nalApplicationNo PCT/EP00/04594 C.(Continuation)DOCUMENTSCONSIDEREDTOBERELEVANT Category Citationofdocument,withindication,whereappropriate,oftherele vantpassagesRelevanttoclaimNo. AJGREIDETAL:"Additionofnitroalkanes1-5,7,8 toortho-halo-nitrobenzenes.Anew synthesisof 4-chloro-7- (trifluoromethyl) quinoline" TETRAHEDRONLETTERS,NL,ELSEVIERSCIENCE PUBLISHERS,AMSTERDAM, vol.8,no.31,1990,pages1093-1096, XP002074108 ISSN:0040-4039 citedintheapplication thewholedocument AWO9728122A(RHONEPOULENCAGROCHIMIE)1-6,10 7August1997(1997-08-07) thewholedocument ADE859009C(BADISCHEANILIN-&1,2 SODA-FABRIK)11December1952(1952-12-11) thewholedocument AEP0527036A(RHONEPOULENCAGRICULTURE)10 10February1993(1993-02-10) citedintheapplication the whole document 1 INTERNATIONALSEARCHREPORT InteanalApplicationNo InformationonpatentfamilyPCT/EP 00/04594 PCT/EP00/04594 PatentdocumentPublication Patent family Publication citedinsearchreportdate member(s)date WO9855446A10-12-1998AU 7607998 A 21-12-1998 AU 7608098 A 21-12-1998 EP 0988276 A 29-03-2000 WO9855437A10-12-1998AU 7806398 A 21-12-1998 EP 1009727 A 21-06-2000 WO9728122A07-08-1997AU 1596197 A 22-08-1997 BR 9707173 A 06-04-1999 CA 2242532 A 07-08-1997 CN 1209804 A 03-03-1999 CZ 9802394 A 11-11-1998 EP 0880498 A 02-12-1998 HU 9900965 A 28-07-1999 JP 2000504000 T 04-04-2000 PL 328574 A 01-02-1999 DE859009CNONE EP0527036A10-02-1993AT 144981 T 15-11-1996 AU 655648 B 05-01-1995 AU 2073092 A 11-02-1993 BG 61568 B 30-12-1997 BG 96747 A 24-03-1994 BR 9203100 A 30-03-1993 CA 2075348 A 06-02-1993 CN 1069268A,B 24-02-1993 CN 1149582 A 14-05-1997 CZ 284801 B 17-03-1999 DE 69215028 D 12-12-1996 DE 69215028 T 07-05-1997 DK 527036 T 25-11-1996 EG 19908 A 31-05-1996 ES 2094878 T 01-02-1997 FI 923515 A 06-02-1993 GR 3022068 T 31-03-1997 HK 1003790 A 06-11-1998 HR 920256 A 31-10-1995 HU 61734 A 01-03-1993 IL 102675 A 31-10-1996 JP 5202008 A 10-08-1993 KR 239189 B 01-02-2000 MX 9204522 A 01-08-1993 NZ 243817 A 24-02-1995 RO 111678 B 30-12-1996 SI 9200163 A 31-03-1993 SK 241292 A 08-02-1995 RU 2065854 C 27-08-1996 TR 27328 A 12-01-1995 ZA 9205872 A 01-03-1993 ZW 12692 A 15-09-1993

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