IP Library Granted Patent US 11,512,044
Granted Patent B2
US 11,512,044 · App. 16/768,570 · Granted Nov 29, 2022

Method for preparing salicylamine acetate

Inventor: Ling Long (Shanghai, CN)
Assignee: TSI GROUP CO., LTD.
C07C231/10C07C235/34
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Quick Facts
Patent No.
US 11,512,044
App. No.
16/768,570
Granted
Nov 29, 2022
Kind
B2
Abstract

Disclosed is a method for preparing salicylamine acetate. The method comprises the steps of: (1) carrying out amino protection on salicylaldehyde having a structure represented by formula 1 to obtain a compound having a structure represented by formula 2; and (2) carrying out acid hydrolysis to the compound having a structure represented by formula 2 and then reacting the acid-hydrolyzed compound with acetic acid to obtain salicylamine acetate.

Claims (15)

1. A method for preparing salicylamine acetate, wherein the method comprises steps of:

(1) subjecting salicylaldehyde of Structural Formula 1:

to amino protection to obtain a compound of Structural Formula 2:

wherein the amino protection is performed with equivalent ratio of tert-butyl carbamate to salicylaldehyde of 1.0-3.0: 1;

and

(2) subjecting the compound of Structural Formula 2 to acid hydrolysis, followed by reaction with acetic acid to obtain salicylamine acetate.

2. The method of claim 1 , wherein the amino protection in Step (1) is performed at a reaction temperature of 0-50° C.

3. The method of claim 1 , wherein the amino protection in Step (1) is performed for a reaction time of 3-18 hours.

4. The method of claim 1 , wherein a reaction solvent selected from the group consisting of tetrahydrofuran, 2-methyltetrahydrofuran, acetonitrile and 1,4-dioxane is used in Step (1).

5. The method of claim 1 , wherein an acid selected from the group consisting of hydrochloric acid, trifluoroacetic acid, hydrobromic acid and sulfuric acid is used for the hydrolysis in Step (2).

6. The method of claim 1 , wherein the acid hydrolysis in Step (2) is performed in the presence of an alcoholic organic solvent.

7. The method of claim 6 , wherein the alcoholic organic solvent is a C1-4 aliphatic alcohol.

8. The method of claim 1 , wherein the reaction with acetic acid in Step (2) is performed at a temperature ranging from room temperature to the reflux temperature of the acetic acid solution.

9. The method of claim 1 , wherein the reaction with acetic acid in Step (2) is performed for a reaction time of 10-24 hours.

10. The method of claim 6 , wherein the alcoholic organic solvent is selected from methanol, ethanol, and n-butanol.

Assignments (2)
CHANGE OF NAME Recorded May 12, 2022
From: JIANGYIN TSI PHARMACEUTICAL CO., LTD.
To: TSI GROUP, CO. LTD.
Reel/Frame 059985/0402 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2020
From: LONG, LING
To: JIANGYIN TSI PHARMACEUTICAL CO., LTD
Reel/Frame 054600/0293 →
Priority Claims (1)
CN 201711221319.7 · Nov 28, 2017 · national
Continuity (1)
Related Publication 20210053907A1 · Feb 25, 2021
Cited By (1)
US 12,668,566