Dimethylformamide dimethyl acetal → Methyl 4-[(E)-2-(dimethylamino)vinyl]-5-nitropyridine-2-carboxylate

HRID 2377051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377051
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>C(#N)C.CN(C=O)C>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1

Komponenten

5

Edukt 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 20717632Methyl 4-methyl-5-nitropyridine-2-carboxylate2×

Produkt 1

HCID 86602115Methyl 4-[(E)-2-(dimethylamino)vinyl]-5-nitropyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Method 1. A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (3.5 g, 17.8 mmol), dimethylformamide dimethylacetal (DMF-DMA) (3.6 ml, 1.5 eq) in acetonitrile (35 mL) was heated in a microwave at 140° C. for 20 min. The solvent was removed. The residue (5.1 g) was carried onto the next step without further purification. Method 2. A mixture of methyl 4-methyl-5-nitropyridine-2-carboxylate (39.5 g, 0.19 mol) and DMF-DMA (30.6 g, 0.26 mol, 1.35 eq) in DMF (470 mL) was heated to 90° C. for 30 min. The solvent was removed in vacuo. The residue (78 g) was used without further purification in the next step.

Aufarbeitung

  1. customThe solvent was removed
  2. customThe residue (5.1 g) was carried onto the next step without further purification
  3. temperaturewas heated to 90° C. for 30 min
  4. customThe solvent was removed in vacuo
  5. customThe residue (78 g) was used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-55ff803c745e41c0bfa4cf019e266ff6
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468375B2

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