Ammonium Chloride → 3-(Trifluoromethoxy)pyridin-2-amine

Temperature

70 °C

To a stirred solution of 2-nitro-3-(trifluoromethoxy)pyridine (370 mg, 1.78 mmol) in ethanol (5 mL) were added aqueous ammonium chloride (951 mg, 17.78 mmol, in 10 mL of water) and iron powder (993 mg, 17.78 mmol). The reaction mixture was heated to 70° C. for 2 h. After cooling down the reaction mixture was filtered and the solid was washed with ethyl acetate. The mother liquid was concentrated to dryness in vacuo. The residue was diluted with water and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was used in next step directly without further purification (250 mg, 79%): 1H NMR (400 MHz, DMSO-d6) δ 7.93-7.91 (m, 1H), 7.48-7.46 (m, 1H), 6.59-6.56 (m, 1H), 6.35 (brs, 2H).

1. temperatureAfter cooling down the reaction mixture
2. filtrationwas filtered
3. washthe solid was washed with ethyl acetate
4. concentrationThe mother liquid was concentrated to dryness in vacuo
5. additionThe residue was diluted with water
6. extractionextracted with ethyl acetate (3×15 mL)
7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
8. concentrationconcentrated to dryness in vacuo
9. customThe residue was used in next step directly without further purification (250 mg, 79%)

ORD record

ord-96f4d3aae38045bf9bb9b737d394ae85

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365583B2