IP Library › Granted Patent US 12,187,664
Granted Patent B2
US 12,187,664 · App. 18/190,244 · Granted Jan 7, 2025

High purity 2-naphthylacetonitrile and method for producing same

Inventors: Masaki Nagahama (Chiyoda, JP); Daiki Okado (Chiyoda, JP); Hirotsugu Taniike (Chiyoda, JP)
Assignee: API CORPORATION
C07C253/22C07C255/33
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Quick Facts
Patent No.
US 12,187,664
App. No.
18/190,244
Granted
Jan 7, 2025
Kind
B2
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.

Claims (15)

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.

Assignments (1)
ADDRESS CHANGE Recorded Apr 13, 2023
From: API CORPORATION
To: API CORPORATION
Reel/Frame 063325/0621 →
Priority Claims (1)
JP 2019-196782 · Oct 29, 2019 · national
Continuity (2)
Continuation 17295222
Related Publication 20230227400A1 · Jul 20, 2023
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