IP Library Granted Patent US 9,150,538
Granted Patent B2
US 9,150,538 · App. 14/347,468 · Granted Oct 6, 2015

Method for producing 4, 4-difluoro-3,4-dihydroisoquinoline derivatives

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Quick Facts
Patent No.
US 9,150,538
App. No.
14/347,468
Granted
Oct 6, 2015
Kind
B2
Abstract

Provided is a simple and efficient method for the large-scale production of a 4,4-difluoro-3,4-dihydroisoquinoline derivative. In the method for producing a 4,4-difluoro-3,4-dihydroisoquinoline derivative represented by general formula (1): a compound represented by general formula (2): is reacted with hydrogen fluoride.

Claims (7)

1. A method for producing a compound represented by general formula (1):

wherein R1 and R2 independently represent an unsubstituted or substituted alkyl group having 1 to 6 carbon atoms or R1 and R2 together with the carbon atom to which they are bound form an unsubstituted or substituted cycloalkyl group having 3 to 10 carbon atoms, X represents a halogen atom, unsubstituted or substituted alkyl group having 1 to 6 carbon atoms or unsubstituted or substituted alkoxy group having 1 to 6 carbon atoms, n represents an integer of 0 to 4, Y represents a halogen atom, unsubstituted or substituted alkyl group having 1 to 6 carbon atoms or unsubstituted or substituted alkoxy group having 1 to 6 carbon atoms, and m represents an integer of 0 to 6, comprising reacting a compound represented by general formula (2):

wherein R1, R2, X, Y, n and m are the same as previously defined, with hydrogen fluoride.

2. The method for producing a compound represented by general formula (1) described in claim 1 , wherein the compound represented by general formula (2) is obtained by reacting a compound represented by general formula (3):

wherein R1, R2, X, Y, n and m are the same as in claim 1 , with a brominating agent.

3. The method for producing a compound represented by general formula (1) described in claim 1 , wherein R1 and R2 independently represent an unsubstituted or substituted alkyl group having 1 to 6 carbon atoms, n=0 and m=0.

4. The method for producing a compound represented by general formula (1) described in claim 2 , wherein R1 and R2 independently represent an unsubstituted or substituted alkyl group having 1 to 6 carbon atoms, n=0 and m=0.

Assignments (2)
CHANGE OF NAME Recorded Feb 7, 2024
From: MITSUI CHEMICALS AGRO, INC.
To: MITSUI CHEMICALS CROP & LIFE SOLUTIONS, INC.
Reel/Frame 066508/0493 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2014
From: UMETANI, HIDEKI; KONDO, NOBUHIRO; KAJINO, FUMIE
To: MITSUI CHEMICALS AGRO, INC.
Reel/Frame 032532/0082 →