Title:
HIGH PURITY 2-NAPHTHYLACETONITRILE AND METHOD FOR PRODUCING SAME
Document Type and Number:
WIPO Patent Application WO/2021/085468
Kind Code:
A1
Abstract:
The present invention provides: high purity 2-naphthylacetonitrile which contains few impurities and is useful as a raw material or intermediate for synthesizing a variety of medicinal products, agrochemicals and chemical products; and a method for producing same. The high purity 2-naphthylacetonitrile has a HPLC purity of 95% or more by area and is such that the content of naphthalene compounds represented by formulae (a) to (j) is a prescribed areal percentage or less. The method for producing high purity 2-naphthylacetonitrile is characterized by including step 1 and step 2 below. Step 1 is a step for hydrolyzing an amide compound, which is obtained by subjecting 2'-acetonaphthone to the Willgerodt reaction in the presence of additives if necessary, and then obtaining 2-naphthylacetic acid. Step 2 is a step for obtaining 2-naphthylacetonitrile by reacting the 2-naphthylacetic acid obtained in step 1, a halogenating agent and sulfamide in an organic solvent in the presence of a catalyst if necessary.
Inventors:
NAGAHAMA MASAKI (JP)
OKADO DAIKI (JP)
TANIIKE HIROTSUGU (JP)
OKADO DAIKI (JP)
TANIIKE HIROTSUGU (JP)
Application Number:
PCT/JP2020/040413
Publication Date:
May 06, 2021
Filing Date:
October 28, 2020
Export Citation:
Assignee:
API CORP (JP)
International Classes:
C07C253/00; C07C255/33
Domestic Patent References:
| WO2019208807A1 | 2019-10-31 | |||
| WO2007016155A2 | 2007-02-08 | |||
| WO2015089111A1 | 2015-06-18 | |||
| WO2015102826A1 | 2015-07-09 |
Foreign References:
| JP2009531277A | 2009-09-03 | |||
| JPS61268650A | 1986-11-28 | |||
| JP2019018065W | 2019-04-26 |
Other References:
WU GUOJIAO, DENG YIFAN, WU CHAOQIANG, ZHANG YAN, WANG JIANBO: "Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, vol. 53, no. 39, 22 September 2014 (2014-09-22), pages 10510 - 10514, XP055932201, ISSN: 1433-7851, DOI: 10.1002/anie.201406765
KANGANI,C.O. ET AL.: "Controlled conversion of phenylacetic acids to phenylacetonitriles or benzonitriles using bis(2-methoxyethyl)aminosulfur trifluoride", TETRAHEDRON LETTERS, vol. 49, no. 5, 2008, pages 914 - 918, XP022413175, DOI: 10.1016/j.tetlet.2007.11.090
HUBER,V.J. ET AL.: "Preparation of nitriles from carboxylic acids: a new, synthetically useful example of the Smiles rearrangement", TETRAHEDRON, vol. 54, no. 32, 1998, pages 9281 - 9288, XP004127405, DOI: 10.1016/S0040-4020(98)00581-X
PRICE CHARLES C, ZOMLEFER JACK: "A STUDY OF THE SYNTHESIS OF YINYLPYRIMIDINES", J.ORG.CHEM., vol. 14, no. 2, 1 January 1949 (1949-01-01), pages 210 - 215, XP055932205
M. MUJAHID ALAM, SRINIVAS R. ADAPA: "A Facile Synthesis of Phenylacetic Acids via Willgerodt-Kindler Reaction Under PTC Condition", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 33, no. 1, 1 March 2003 (2003-03-01), US , pages 59 - 63, XP055652307, ISSN: 0039-7911, DOI: 10.1081/SCC-120015559
A HULKENBERG, J.J.TROOST: "An efficient one-pot synthesis of nitriles from acid chlorides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 23, no. 14, 1 January 1982 (1982-01-01), Amsterdam , NL , pages 1505 - 1508, XP055751666, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)87144-0
TETRAHEDRON LETTERS, vol. 56, 2015, pages 2054 - 2058
TETRAHEDRON LETTERS, vol. 23, no. 14, 1982, pages 1505 - 1508
SYNTHETIC COMMUNICATIONS, vol. 33, 2003, pages 59 - 63
See also references of EP 3950664A4
KANGANI,C.O. ET AL.: "Controlled conversion of phenylacetic acids to phenylacetonitriles or benzonitriles using bis(2-methoxyethyl)aminosulfur trifluoride", TETRAHEDRON LETTERS, vol. 49, no. 5, 2008, pages 914 - 918, XP022413175, DOI: 10.1016/j.tetlet.2007.11.090
HUBER,V.J. ET AL.: "Preparation of nitriles from carboxylic acids: a new, synthetically useful example of the Smiles rearrangement", TETRAHEDRON, vol. 54, no. 32, 1998, pages 9281 - 9288, XP004127405, DOI: 10.1016/S0040-4020(98)00581-X
PRICE CHARLES C, ZOMLEFER JACK: "A STUDY OF THE SYNTHESIS OF YINYLPYRIMIDINES", J.ORG.CHEM., vol. 14, no. 2, 1 January 1949 (1949-01-01), pages 210 - 215, XP055932205
M. MUJAHID ALAM, SRINIVAS R. ADAPA: "A Facile Synthesis of Phenylacetic Acids via Willgerodt-Kindler Reaction Under PTC Condition", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 33, no. 1, 1 March 2003 (2003-03-01), US , pages 59 - 63, XP055652307, ISSN: 0039-7911, DOI: 10.1081/SCC-120015559
A HULKENBERG, J.J.TROOST: "An efficient one-pot synthesis of nitriles from acid chlorides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 23, no. 14, 1 January 1982 (1982-01-01), Amsterdam , NL , pages 1505 - 1508, XP055751666, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)87144-0
TETRAHEDRON LETTERS, vol. 56, 2015, pages 2054 - 2058
TETRAHEDRON LETTERS, vol. 23, no. 14, 1982, pages 1505 - 1508
SYNTHETIC COMMUNICATIONS, vol. 33, 2003, pages 59 - 63
See also references of EP 3950664A4
Attorney, Agent or Firm:
TAKASHIMA, Hajime (JP)
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