Method for producing 2-amino-substituted benzaldehyde compound

Patent metadata

Field	Value
Publication number	US-10047037-B2
Application number	US-201515504499-A
Country	US
Kind code	B2
Filing date	Aug 25, 2015
Priority date	Sep 1, 2014
Publication date	Aug 14, 2018
Grant date	Aug 14, 2018

Abstract

The present invention provides a method for producing a benzaldehyde in which an amino group is bonded in the 2 position, a halogeno group or an alkoxy group is bonded in the 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions, the method including: preparing a benzaldehyde in which a halogeno group or an alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of the 4, 5, and 6 positions so that a lithiation reaction is most active at the 2 position; acetal-protecting a formyl group in the benzaldehyde; sequentially performing lithiation, azidation, and amination of the 2 position; and the performing acetal deportection.

First claim

The invention claimed is:

1. A method for producing a benzaldehyde in which an amino group is bonded in a 2 position, a halogeno group or an alkoxy group is bonded in a 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of 4, 5, and 6 positions, the method comprising:
preparing a benzaldehyde in which the halogeno group or the alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and the hydrogen atom, the alkyl group, the halogeno group, the alkoxy group, or the cyano group is bonded independently in each of the 4, 5, and 6 positions so that a lithiation reaction is most active at the 2 position (hereinafter, abbreviated as 2-unsubstituted benzaldehyde (I-1));
acetal-protecting a formyl group in the 2-unsubstituted benzaldehyde (I-1);
sequentially performing lithiation, azidation, and amination of the 2 position; and
subsequently performing acetal deportection.

2. A method for producing a benzaldehyde in which an amino group is bonded in a 2 position, a halogeno group or an alkoxy group is bonded in a 3 position, and a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group is bonded independently in each of 4, 5, and 6 positions, the method comprising:
preparing a benzaldehyde in which the halogeno group or the alkoxy group is bonded in the 3 position, a hydrogen atom is bonded in the 2 position, and the hydrogen atom, the alkyl group, the halogeno group, the alkoxy group, or the cyano group is bonded independently in each of the 4, 5, and 6 positions so that a boration reaction is most active at the 2 position (hereinafter, abbreviated as 2-unsubstituted benzaldehyde (I-2));
acetal-protecting a formyl group in the 2-unsubstituted benzaldehyde (1-2);
sequentially performing boration, azidation, and amination of the 2 position; and
subsequently performing acetal deportection.

3. The method according to claim 1 , wherein the 2-unsubstituted benzaldehyde (I-1) or (I-2) is a compound of formula (I-12):

(in the formula (I-12),
R 3 represents a halogeno group or an alkoxy group,
R 4 , R 5 , and R 6 each independently represent a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group,
wherein in a case where R 4 is a hydrogen atom, R 5 is a hydrogen atom, an alkyl group, or a cyano group,
in a case where R 5 is a hydrogen atom, at least one of R 4 and R 6 is a hydrogen atom, an alkyl group, or a cyano group, and
in a case where R 6 is a hydrogen atom, R 5 is a hydrogen atom, an alkyl group, or a cyano group).

4. The method according to claim 2 , wherein the 2-unsubstituted benzaldehyde (I-1) or (I-2) is a compound of formula (I-12):

(in the formula (I-12),
R 3 represents a halogeno group or an alkoxy group,
R 4 , R 5 , and R 6 each independently represent a hydrogen atom, an alkyl group, a halogeno group, an alkoxy group, or a cyano group,
wherein in a case where R 4 is a hydrogen atom, R 5 is a hydrogen atom, an alkyl group, or a cyano group,
in a case where R 5 is a hydrogen atom, at least one of R 4 and R 6 is a hydrogen atom, an alkyl group, or a cyano group, and
in a case where R 6 is a hydrogen atom, R 5 is a hydrogen atom, an alkyl group, or a cyano group).

Assignees

• Nippon Soda Co

Inventors

• Kobayashi Shinichi

Classifications

• C07D317/28

  Radicals substituted by nitrogen atoms (nitro radicals C07D317/16) · CPC title

• C07C221/00 Primary

  Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C07C223/06 Primary

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• C07D317/16

  Radicals substituted by halogen atoms or nitro radicals · CPC title

• C07B51/00

  Introduction of protecting groups or activating groups, not provided for in the preceding groups · CPC title