Dimethylformamide dimethyl acetal → HCID 10921384, compound

HRID 1472940Notes

Reaction equation

HRID 1472940 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][N:12]([CH:14](OC)OC)[CH3:13]>CN(C=O)C>[CH3:11][N:12]([CH3:14])/[CH:13]=[CH:1]/[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 3293602-Methyl-3-nitropyridine

Product 1

HCID 10921384HCID 10921384, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  1. customAfter evaporating the solvent (E)-N,N-Dimethyl-2-(3-nitropyridin-2-yl)ethenamine

Sources & evidence

ORD record
ord-5c3446ba5a0f444e8198e1e032553317
Source dataset
uspto-grants-2015_04
Patent number
US09012659B2

Reaction notes

Loading…