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

HRID 2393441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393441
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 53811652N,N-Dimethyl-2-(2-acetylamino-5-nitropyridin-4-yl)ethenamineAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9dbf4cbab6ee4efca335239cf1642829
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807857

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