ChemicalBook CAS DataBase List 5-Amino-3-(trifluoromethyl)picolinonitrile

5-Amino-3-(trifluoromethyl)picolinonitrile synthesis

13synthesis methods

Product Name:5-Amino-3-(trifluoromethyl)picolinonitrile
CAS Number:573762-62-6
Molecular formula:C7H4F3N3
Molecular Weight:187.12

5-Nitro-3-trifluoroMethylpyridine-2-carbonitrile

573762-57-9
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5-Amino-3-(trifluoromethyl)picolinonitrile

573762-62-6
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Yield:573762-62-6 95%

Reaction Conditions:

with hydrogenchloride;iron in water;ethyl acetateReflux;

Steps:

5.1.5. 2-Cyano-5-amino-3-(trifluoromethyl)pyridine (9)
To the solution of intermediate 8 (17.6 g, 0.08 mol) in EtOH andEtOAc (1:1, 100 mL), the iron powder (22.7 g, 0.40 mol) and HCl(1 mL) was added. The reaction mixture was heated to reflux andthe progress of the reaction was monitored by TLC. After 12 h, thereaction mixture was filtered using diatomite and the filtrate wasconcentrated under reduced pressure. The crude was added EtOAcand saturated aqueous Na2CO3 solution. The water phase wasextracted with EtOAc. Then the combined organic phase waswashed with saturated brine, dried over Na2SO4, filtered andconcentrated to give the desired product, as brown solid in 95%yield. HRMS (ESI): m/z, calcd for C7H5F3N3 [M H], 188.0430;found: 188.0432.

References:

Bian, Jinlei;Chen, Xijing;Du, Qianming;Ge, Raoling;Li, Yan;Li, Zhiyu;Lu, Xiaoyu;Meng, Ying;Wang, Jubo;Wu, Hongxi;Xu, Xi;Xue, Siqi;Yang, Yong;Zhao, Zhili [European Journal of Medicinal Chemistry,2020,vol. 192]

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