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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2396312Generated: October 27, 2026

Sodium Hydroxide → 3-Chloro-5-(trifluoromethyl)-2-pyridinamine

https://huagongshe.com/reaction/2396312

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantN-ChlorophthalimideHCID 18997—
Reactant2-Amino-5-(trifluoromethyl)pyridineHCID 735862—
Reactant2-Chloroamino-5-trifluoromethylpyridineHCID 18988854—
SolventTolueneHCID 1140—
Product3-Chloro-5-(trifluoromethyl)-2-pyridinamineHCID 60724889%

Reaction Steps

Into the same 300 ml four-necked flask as used in Example 1, 16.2 g (0.1 mol) of 2-amino-5-trifluoromethylpyridine, 20.9 g (0.115 mol) of N-chlorophthalimide and 150 g of toluene were added, and the reaction was carried out at 80° C. for one hour under heating with stirring. During the reaction, formation of 2-chloroamino-5-trifluoromethylpyridine was confirmed. After completion of the reaction, the reaction mixture was cooled to room temperature, and 50 g of a 25% sodium hydroxide aqueous solution was added thereto and stirred. An aqueous layer and an oil layer were separated. A 20% hydrochloric acid aqueous solution was added to the oil layer, and the mixture was stirred. An aqueous layer and an oil layer were separated again. The aqueous layer was neutralized with a 25% sodium hydroxide aqueous solution. Precipitated slightly yellow crystals were collected by filtration and dried to obtain 17.5 g 2-amino-3-chloro-5-trifluoromethylpyridine (purity as measured by liquid chromatography: 97%, yield: 86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05491239
Source datasetuspto-grants-1996_02
ORD IDord-a08d5a41fe1741af80931e4fcd152e5d
Source noteuspto-grants-1996_02