Stannous chloride dihydrate → 2-Chloro-5-(trifluoromethyl)pyridin-3-amine

Temperature

80 °C

To a solution of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1.87 g) in ethyl acetate (40 mL) was added tin(II) chloride dihydrate (8.22 g), and the mixture was stirred at 80° C. for 2 hours. After cooling, to the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution, and the mixture was vigorously stirred at room temperature and filtered through a celite pad. The residue was washed with ethyl acetate. The filtrate was combined with the washings, washed successively with an aqueous saturated sodium hydrogencarbonate solution, water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was triturated with n-hexane to give 3-amino-2-chloro-5-(trifluoromethyl)pyridine (0.99 g) as a pale yellow powder.

1. temperatureAfter cooling, to the reaction mixture
2. stirringthe mixture was vigorously stirred at room temperature
3. filtrationfiltered through a celite pad
4. washThe residue was washed with ethyl acetate
5. washwashed successively with an aqueous saturated sodium hydrogencarbonate solution, water and brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe resultant residue was triturated with n-hexane

ORD record

ord-0b49a8f9634c4bbb99bdcd65a06e85d1

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998956B2