Title:
METHOD FOR PRODUCING 1,2-DIHYDROQUINOLINE SYNTHETIC INTERMEDIATE
Document Type and Number:
WIPO Patent Application WO/2014/098046
Kind Code:
A1
Abstract:
A method for producing a compound represented by formula (2) or a salt thereof, characterized in that a compound represented by formula (1) or a salt thereof is reacted with 2,2-dialkoxypropane or isopropenyl alkyl ether in the presence of (A) an acid selected from the group consisting of p-toluenesulfonic acid, pyridinium-p-toluenesulfonate, hydrobromic acid, and pyridine hydrobromide, and/or (B) a base selected from the group consisting of pyridine and N,N-dimethylaniline, and (C) water. This production method is suited to the industrial production of a synthetic intermediate of a 1,2-dihydroquinoline derivative having glucocorticoid receptor-binding activity.
Inventors:
OHNO ATSUSHI (JP)
KUDOU KAZUHIRO (JP)
KATSUHIRA TAKESHI (JP)
KUDOU KAZUHIRO (JP)
KATSUHIRA TAKESHI (JP)
Application Number:
PCT/JP2013/083666
Publication Date:
June 26, 2014
Filing Date:
December 16, 2013
Export Citation:
Assignee:
SANTEN PHARMACEUTICAL CO LTD (JP)
KYOWA HAKKO BIO CO LTD (JP)
KYOWA HAKKO BIO CO LTD (JP)
International Classes:
C07D491/052; C07C229/60; C07D215/48; C07D311/78
Domestic Patent References:
| WO2008059865A1 | 2008-05-22 | |||
| WO2013108921A1 | 2013-07-25 |
Other References:
ANDREW V. ANZALONE, ET AL.: "ACommon Diaryl Ether Intermediate for the Gram-Scale Synthesis of Oxazine and Xanthene Fluorophores", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 52, no. 2, 7 January 2013 (2013-01-07), pages 650 - 654
J.S. YADAV, ET AL.: "Bi(OTf)3-catalyzed condensation of 2,2-DMP with aromatic amines: A rapid synthesis of 2,2,4-trimethyl-1,2-dihydroquinolines", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 271, no. 1-2, 18 June 2007 (2007-06-18), pages 161 - 163, XP022070243
THEOCLITOU M-E; ROBINSON L A: "Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via a modified Skraup reaction", TETRAHEDRON LETTERS, vol. 43, no. 21, 20 May 2002 (2002-05-20), pages 3907 - 3910, XP004352436
RANU B C; HAJRA A; DEY S S; JANA U: "Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions", TETRAHEDRON, vol. 59, no. 6, 3 February 2003 (2003-02-03), pages 813 - 819, XP004404939
J.S. YADAV, ET AL.: "Bi(OTf)3-catalyzed condensation of 2,2-DMP with aromatic amines: A rapid synthesis of 2,2,4-trimethyl-1,2-dihydroquinolines", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 271, no. 1-2, 18 June 2007 (2007-06-18), pages 161 - 163, XP022070243
THEOCLITOU M-E; ROBINSON L A: "Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via a modified Skraup reaction", TETRAHEDRON LETTERS, vol. 43, no. 21, 20 May 2002 (2002-05-20), pages 3907 - 3910, XP004352436
RANU B C; HAJRA A; DEY S S; JANA U: "Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions", TETRAHEDRON, vol. 59, no. 6, 3 February 2003 (2003-02-03), pages 813 - 819, XP004404939
Attorney, Agent or Firm:
TSUJII Koichi et al. (JP)
辻居 Koichi (JP)
辻居 Koichi (JP)
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