Dimethylformamide dimethyl acetal → N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamine

HRID 2393441Notes

Reaction equation

HRID 2393441 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=1)(=[O:3])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:17][N:18]([CH3:20])[CH:19]=[CH:11][C:9]1[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamide

Product 1

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-acetylamino-4-methyl-5-nitropyridine (33.8 g, 0.173 mol) in dry DMF (300 mL) was added dimethylformamide dimethyl acetal (50.7 mL, 0.381 mol) and the mixture heated at 90° C. for 90 min. The solvent was evaporated in vacuo using toluene as an azeotrope. The residue was triturated with ether and the solid collected by filtration to give the title compound (33 g, 76%) as an orange solid. mp 193°-196° C. 1H NMR (250 MHz, CDCl3) δ 2.23 (3H, s), 3.04 (6H, s), 6.12 (1H, d, J=13.1Hz), 7.43 (1H, d, J=13.1Hz), 8.17 (1H, br s), 8.27 (1H, s) and 8.83 (1H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was triturated with ether
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-9dbf4cbab6ee4efca335239cf1642829
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…