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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 9856208 B1

PDFFull Text
Date of Patent:
Jan. 02, 2018

Filed:

Sep. 02, 2016

Method for producing an arene with an aromatic c—n bond ortho to an aromatic c—o bond

Applicant:

The Royal Institution for the Advancement of Learning/mcgill University, Montreal, CA;

Inventors:

Jean-Philip Lumb, Montreal, CA;

Kenneth V. N. Esguerra, Toronto, CA;

Assignee:

The Royal Institution for the advancement of Learning/McGill University, Montreal, CA;

Attorney:

Isabelle Pelletier

Primary Examiner:

Kahsay Habte

Int. Cl.
CPC ...
C07C 249/02 (2006.01); C07C 213/08 (2006.01); C07C 45/29 (2006.01); C07D 265/36 (2006.01); C07D 263/56 (2006.01); C07C 46/08 (2006.01); C07F 7/00 (2006.01); C07F 7/08 (2006.01);
U.S. Cl.
CPC ...
C07C 249/02 (2013.01); C07C 46/08 (2013.01); C07C 213/08 (2013.01); C07D 263/56 (2013.01); C07D 265/36 (2013.01); C07F 7/00 (2013.01); C07F 7/0812 (2013.01); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05); C07C 2602/10 (2017.05);
Abstract

A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:

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