Process for the preparation of 7-substituted...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

10478020

ABSTRACT:
Process for the preparation of compounds of formula (I) wherein R is halogen, R1O1R1S(O)nor (R1)2NC(X)O; R1is C1-C8alkly, aryl-C1-C8alkyl, C1-C8haloalkyl or aryl; n is 0, 1, 2 or 3; X is O or S; and R2is hydrogen, C1-C4alkyl or C1-C4haloalkyl, in which process, in a solvent, (1) an aniline derivative of formula (IV) wherein R is as defined above, and R3is C1-C5alkyl or C1-C5haloalkyl, is diazotised in the presence of a mineral acid to form the corresponding diazonium salt of formul (II) wherein R and R3are as defined above, Am−is an anion, and m is 1 or 2, (2) the resulting diazonium salt of formula (II) is carbonylated in the presence of a catalyst, CO and optionally a buffer, to form a benzoic acid derivative of formula (III) wherein R and R3are as defined above, and (3) the benzoic acid derivative of formula (III) is then subjected to benzylic lactonisation in the ortho-position alkyl chain R3in the presence of a free-radical initiator and a halogenating agent.

REFERENCES:
patent: 1112529 (1961-08-01), None
patent: 2060063 (1971-06-01), None
patent: 9105781 (1991-05-01), None
patent: 9619443 (1996-06-01), None
Kayser, MM ‘The internal steric push-effect: its consequences on the reactivity of carbony functions in 3-substituted phthalic anhydrides’ CA 111:38768 (1989).
Epsztajn et al. STN ACCESSION No. 1993:147272; Document No. 118:147272;Abstract of Monatshefte fuer Chemie (1992), 123(12), 1125-34.
Nagira Kazuhiko et al.: Journal of Organic Chemistry, vol. 45, No. 12, 1980, pp. 2365-2368.
Drozd et al.: Journal of Organic Chemistry USSR (English Translation), vol. 9, 1973, p. 2564.
Mongin F. et al.: “Reagent-Modulated Optional Site Selectivities: The Metalation of o-, m- and p- Halobenzotrifluorides”, Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 37, No. 16, Apr. 15, 1996, pp. 2767-2770.
Ino, A. et al.: “Total Synthesis of the Antimycoplasma Antibiotic Micacocidin”, Tetrahedron Letters, Elsevier Science Publishers, Amsterdam, NL, vol. 39, No. 32, May 21, 1998, pp. 3509-3512.
Lüthy, C. et al.: “7-(4,6-Demethoxypyrimidinyl)oxy- and -thiophthalides as novel herbicides: Part 1. CGA 279 233: a new grass-killer for rice”, Pest Management Science, Elsevier, Barking, GB, vol. 57, Mar. 16, 2001, pp. 205-224.
Bunnett, J. F. et al: “Steric Acceleration of the Lactonization of 2-(Hydroxymethyl) Benzoic Acids”, Journal of The American Chemical Society, American Chemical Society, Washington, D.C., vol. 87, No. 10, May 1965, pp. 2214-2220.
Soucy, D. et al.: “On the Regioselectivity of Mehtal Hydride Reductions of 3-Substituted Phthalic Anhydrides”, Journal of Organic Chemistry, American Chemical Society, Easton, US, vol. 52, 1987, pp. 129-134.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the preparation of 7-substituted... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of 7-substituted..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of 7-substituted... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3840509

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.