N-Methylethylenediamine → 1-Methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-one

HRID 1772078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772078
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:17])C(OCC)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:18][NH:19][CH2:20][CH2:21][NH2:22]>CO>[CH3:18][N:19]1[CH2:20][CH2:21][N:22]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[C:11]1=[O:17]

Komponenten

4

Edukt 2

HCID 8014N-MethylethylenediamineHCID 15716402Ethyl 4-nitrophenylpyruvate

Produkt 1

HCID 666138231-Methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-oneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with ethyl 4-nitrophenylpyruvate (5.00 g, 22.4 mmol) and anhydrous methanol (112 mL). The resulting solution was cooled to 0° C. with an ice bath, and N-methylethylenediamine (1.66 g, 22.4 mmol) was added dropwise. After addition was complete, the bath was removed and the reaction was stirred at room temperature for 18 h. After this time the reaction was concentrated under reduced pressure. The residue was purified by column chromatography to afford 1-methyl-3-(4-nitrophenyl)-5,6-dihydropyrazin-2(1H)-one (102h) in 20% yield (1.02 g) as a yellow solid: mp 191-192° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.26 (d, 2H, J=6.9 Hz), 8.05 (d, 2H, J=7.2 Hz), 3.94 (t, 2H, J=6.3 Hz), 3.55 (t, 2H, J=6.3 Hz), 3.02 (s, 3H); MS (ESI+) m/z 234.1 (M+H).

Aufarbeitung

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. additionAfter addition
  4. customthe bath was removed
  5. concentrationAfter this time the reaction was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-78f75b24a5624e278b4817b85c3d926a
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249123B2

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