Acetonitrile → N,N-dimethyl-N'-(5-nitropyridin-2-yl)ethane-1,2-diamine

To a round bottom flask, charged with 2-chloro-5-nitropyridine (1.0 g, 6.3 mmol), dimethylethane-1,2-diamine (0.55 g, 6.3 mmol), triethylamine (0.63 g, 6.3 mmol) and acetonitrile (10 mL). The resulting reaction mixture was stirred at ambient temperature for 9 hours. TLC analysis showed no acid remaining so the mixture was diluted with water and extracted with ethylacetate. The organic layer was separated and washed with brine and water, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography using a 95:5 mixture of dichloromethane and methanol as eluent to afford the title product as a brown solid (0.55 g, 42% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.91 (1H, m), 8.09 (2H, m), 6.62 (1H, m), 4.10 (1H, m), 3.50 (2H, m), 3.17 (2H, m), 2.21 (6H, s). MS m/z: 211.14 [M+H]+.

1. customThe resulting reaction mixture
2. extractionextracted with ethylacetate
3. customThe organic layer was separated
4. washwashed with brine and water
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude material was purified by silica gel chromatography
8. additiona 95:5 mixture of dichloromethane and methanol as eluent

ORD-Eintrag

ord-ee90ca04f2c24698bb2e006d8f146ece

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08680139B2