2-(Trifluoromethoxy)aniline → HCID 86655255, compound

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-3-nitropyridine (10.0 g, 51.8 mmol) and 2-(trifluoromethoxy)aniline (18.4 g, 104 mmol) were taken up in ethanol (50 mL) and heated to 100° C. for 48 h in a sealed tube. The reaction mixture was cooled in an ice bath, and the resulting precipitate was collected by vacuum filtration to give an intermediate 6-chloro-3-nitro-N-(2-(trifluoromethoxy)phenyl)pyridin-2-amine, which was dissolved in dioxane (65 mL) and H2O (35 mL). Potassium hydroxide (2.90 g, 51.7 mmol) was added and the reaction mixture was heated to 100° C. for 16 h. After cooling, the pH was adjusted to less than 7 with 1 N HCl. The resulting precipitate was collected by vacuum filtration to give the title compound as a bright yellow solid (5.10 g). LCMS m/z=316.0 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 5.91 (d, J=10.1 Hz, 1H), 7.51 (m, 4H), 8.26 (d, J=10.1 Hz, 1H), 8.50-8.85 (broad s, 1H), 10.78 (broad s, 1H).

Provenance & Evidence