Processes for preparing 6-hydroxy-3,4-dihydroquinolinone,...

Details Processes for preparing 6-hydroxy-3,4-dihydroquinolinone,... Processes for preparing 6-hydroxy-3,4-dihydroquinolinone,...

2005-11-22

2005-11-22

Chang, Ceila (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S312000, C546S158000

Reexamination Certificate

active

06967209

ABSTRACT:
A process for preparing 6-hydroxy-3,4-dihydroquinolinone by intramolecular Friedel-Crafts alkylation of N-(4-methoxyphenyl)-3-chloropropionamide in which an equivalent of N-(4-methoxyphenyl)-3-chloropropionamide is contacted with a Lewis acid in DMSO or a high boiling amide or amine at an elevated temperature of from about 150° C. to about 220° C. is provided. The process produces 6-HQ in high yield and a high state of purity such that it may be used in subsequent reactions toward the preparation of cilostazol without intermediate purification. A process for preparing cilostazol from 6-hydroxy-3,4-dihydroquinolinone prepared by the process and improved processes for preparing N-(4-methoxyphenyl)-3-chloropropionamide are also provided.

REFERENCES:
patent: 3819637 (1974-06-01), Bell
patent: 3994902 (1976-11-01), Bell
patent: 4049715 (1977-09-01), Bell
patent: 4277479 (1981-07-01), Nishi et al.
patent: 4372953 (1983-02-01), Uchida et al.
patent: 5294718 (1994-03-01), Ujiie et al.
patent: 09124605 (1997-03-01), None
patent: 09124605 (1997-05-01), None
patent: 10330262 (1998-12-01), None
patent: 200229944 (1999-02-01), None
patent: 200229944 (2000-08-01), None
Ali A. Khalaf et al., “Modern Friedel-Crafts Chemistry XIII. Intra-and intermolecular cyclization of some carbonyl derivatives under Friedel-Crafts conditions” Bulletin de al Societe Chimique de France, (Jan./Feb. 1984) pp. 11-285-11-291.
Database Casreact on STN Chemical Abstracts, (Columbus OH, USA); No. 102:220723; W. Verboom et al., “The Madelung Synthesis of dihydro-1H-pyrrolo and tetrahydropyrido [1,2-a] indoles under mild conditions” Tetrahedron Lett. (1985).
Database Casreact on STN, Chemical Abstracts, (Columbus, OH, USA); No. 107:39554; W. Verboom et al., “Wynthesis of dihydro-1H-pyrrolo- and tetrahydropyrido [1,2-a] indoles via a modified Madelung”, Tetrahedron (1986).
Database Casreact on STN, Chemical Abstracts, (Columbus, OH, USA); No. 113:23552; Christopher J. Easton et al., “Acyloxylation at the 4-position of azetidin-2-ones”, J. Chem. Soc., Perkin Trans. 1 (1990).
Chem Abstracts Doc. No. 131:257448, Japanese Patent No. 11-269148.
Chem Abstracts Doc. No. 133:11150480k, Japanese Patent No. 2000-229944.
Chem Abstracts Doc. No. 127:34142; Japanese Patent No. 9-124605.

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