Dimethylformamide dimethyl acetal → HCID 10921384, compound

Participants

Reaction Conditions

Reaction Steps

A modified procedure of Cash et al. (Org. Biomol. Chem. 2005, 3. 3701-3706) was used. 2-Methyl-3-nitropyridine (0.7 g, 5.1 mmol) was dissolved in 15 ml dry DMF and stirred under nitrogen. Dimethylformamiddimethylacetal (DMF-DMA) (1.35 ml, 1.22 g, 10.2 mmol) was added dropwise. The reaction was heated to 90° C. for 4 h. After approximately 15 min a deep redish color appeared. After evaporating the solvent (E)-N,N-Dimethyl-2-(3-nitropyridin-2-yl)ethenamine is obtained as a red oil (0.16 g, 0.8 mmol, 73%) which can be used without further purification. 1H NMR (300 MHz, CDCl3) 8.40 (pdd; 3J=1.7 Hz; 3J=4.4 Hz; 1H; H-6); 8.16 (pdd; 3J=1.7 Hz; 3J=8.3 Hz; 1H; H-4); 8.04 (d; 3JAX=12.5 Hz; 1H; H-8); 6.76 (pdd; 3J=4.4 Hz; 3J=8.3 Hz; 1H; H-5); 6.15 (d; 3JAX=12.5 Hz; 1H; H-7); 3.01 (s; 6H; CH3).

Provenance & Evidence