Stannous chloride dihydrate → HCID 58011019, compound

Temperature

2.5 °C

N-(3-aminophenethyl)-2,2,2-trifluoroacetamide hydrochloride (0.27 g, 1.0 mmol) was suspended in 6M HCl (2.0 mL) and cooled thoroughly in an ice bath. This was rapidly stirred while a solution of NaNO2 (73 mg) in H2O (1.0 mL) was added slowly. The mixture was stirred at 0-5° C. for 45 min and was then treated with SnCl2.2H2O (1.3 g, 5.8 mmol) in 6N HCl (4.0 mL). The resulting suspension was stirred at 0-5° C. for 3 h and then carefully quenched with 3N NaOH (15 mL) to pH 7-8. The mixture was diluted with Et2O, filtered through Celite® and the filter cake was washed with H2O and Et2O. The layers of the biphasic filtrate were separated and the aqueous extracted with Et2O (2×). The combined organics extracts were washed with brine (1×), dried (Na2SO4), filtered and evaporated to provided N-(3-hydrazinophenethyl)-2,2,2-trifluoroacetamide as a pale yellow oil (0.18 g, 72% yield), which was used without further purification. MS (ESI) m/z: 248.0 (M+H+).

1. temperaturecooled thoroughly in an ice bath
2. additionwas added slowly
3. stirringThe resulting suspension was stirred at 0-5° C. for 3 h
4. customcarefully quenched with 3N NaOH (15 mL) to pH 7-8
5. additionThe mixture was diluted with Et2O
6. filtrationfiltered through Celite®
7. washthe filter cake was washed with H2O and Et2O
8. customThe layers of the biphasic filtrate were separated
9. extractionthe aqueous extracted with Et2O (2×)
10. washThe combined organics extracts were washed with brine (1×)
11. dry with materialdried (Na2SO4)
12. filtrationfiltered
13. customevaporated

ORD record

ord-7d47949771f74ea2b94e755a3fad9b60

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163756B2