High purity 2-naphthylacetonitrile and method for producing same

Patent metadata

Field	Value
Publication number	US-12187664-B2
Application number	US-202318190244-A
Country	US
Kind code	B2
Filing date	Mar 27, 2023
Priority date	Oct 29, 2019
Publication date	Jan 7, 2025
Grant date	Jan 7, 2025

Abstract

High purity 2-naphthylacetonitrile with fewer impurities that is useful as a starting material or intermediate for the synthesis of various pharmaceutical products, agricultural chemicals, and chemical products, and a production method thereof. A high purity 2-naphthylacetonitrile having an HPLC purity of 2-naphthylacetonitrile of not less than 95 area %, and containing naphthalene compounds represented by the formulas (a)-(j) at a content of a predetermined area % or below. A method for producing high purity 2-naphthylacetonitrile.

First claim

The invention claimed is:

1. A method for producing a high purity 2-naphthylacetonitrile, the method comprising reacting 2-naphthylacetic acid and a halogenating agent, mixing a first reaction starting material comprising an obtained acid halide compound of formula (5), in which X is a halogen atom,

and a second reaction starting material comprising sulfamide at a temperature of from 10° C. to 100° C., and
raising the temperature to from 85° C. to 120° C. to give 2-naphthylacetonitrile.

2. The method according to claim 1 , wherein the first reaction starting material is added to the second reaction starting material at a temperature of from 10° C. to 100° C., and the temperature is raised to a temperature of from 85° C. to 120° C. to give 2-naphthylacetonitrile.

3. The method according to claim 1 , wherein the first reaction starting material is added to the second reaction starting material such that an amount of the acid halide compound is not less than 0.0027 mol/min per 1 mol of the sulfamide.

4. The method according to claim 1 , wherein an amount of the sulfamide is 1 mol to 5 mol per 1 mol of the 2-naphthylacetic acid.

5. The method according to claim 2 , wherein an amount of the sulfamide is 1 mol to 5 mol per 1 mol of the 2-naphthylacetic acid.

6. The method according to claim 2 , wherein the first reaction starting material is added to the second reaction starting material such that an amount of the acid halide compound is not less than 0.0027 mol/min per 1 mol of the sulfamide.

7. The method according to claim 4 , wherein the first reaction starting material is added to the second reaction starting material such that an amount of the acid halide compound is not less than 0.0027 mol/min per 1 mol of the sulfamide.

8. A method for producing high purity 2-naphthylacetonitrile, the method comprising:
subjecting 2′-acetonaphthone to a Willgerodt reaction, optionally in the presence of an additive, to obtain an amide compound;
hydrolyzing the amide compound; and
liberating 2-naphthylacetic acid to give 2-naphthylacetic acid;
mixing a first reaction starting material comprising the liberated 2-naphthylacetic acid, a halogenating agent, and a first organic solvent, and a second reaction starting material comprising sulfamide and a second organic solvent at a temperature in a range of from 10° C. to 100° C.; and
raising the temperature to a range of from 85° C. to 120° C. to give 2-naphthylacetonitrile.

Assignees

• Api Corp

Inventors

• Nagahama Masaki
• Okado Daiki
• Taniike Hirotsugu

Classifications

• C07C303/34

  of amides of sulfuric acids · CPC title

• C07C255/33 Primary

  with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains · CPC title

• C07C253/34 Primary

  Separation; Purification · CPC title

• C07C253/00

  Preparation of carboxylic acid nitriles (of cyanogen or compounds thereof C01C3/00) · CPC title

• C07D295/194

  Radicals derived from thio- or thiono carboxylic acids · CPC title