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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 39602Generated: October 26, 2026

Hydrochloric Acid → 3-(4-Trifluoromethoxy-phenylamino)-isonicotinic acid

https://huagongshe.com/reaction/39602

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant3-Fluoropyridine-4-carboxylic acidHCID 345361—
Reactant4-(Trifluoromethoxy)anilineHCID 600848—
ReactantLithium HexamethyldisilazideHCID 2733832—
SolventTetrahydrofuranHCID 8028—
Product3-(4-Trifluoromethoxy-phenylamino)-isonicotinic acidHCID 576496389%

Reaction Conditions

Temperature-78 °C

Reaction Steps

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethoxy)aniline (62.8 mg, 0.354 mmol) was added to 2 ml dry THF and the mixture was cooled to −78° C. LiHMDS (1M in THF, 1.24 ml) was added and the mixture was allowed to warm to room temperature over night. Hydrochloric acid (1M in methanol, 5 ml) was added and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 9.5 mg (32 μmol; 9% yield) of pure desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08524911B2
Source datasetuspto-grants-2013_09
ORD IDord-68aa3eff66cc499abf1b2121278b6d86
Source noteuspto-grants-2013_09