Sodium Hydroxide → 2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

HRID 440871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440871
[N+]([O-])(O)=O.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]([NH2:18])=[NH:17].CN(C)[CH:21]=[CH:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O.[OH-].[Na+]>C(O)(C)C>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[NH:15][C:16]1[N:18]=[C:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][N:17]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178426711HCID 178426711, Verbindung

Produkt 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

248.2 g (0.96 mol) of 2-methyl-5-nitrophenylguanidine nitrate are added to a solution of 170 g (0.96 mol) of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one in 2.0 liters of isopropanol. After the addition of 42.5 g of sodium hydroxide, the reddish suspension is boiled at reflux for 12 hours. After cooling to 0°, filtration, washing with 2.0 liters of isopropanol and 3×400 ml of methanol and drying, there is obtained N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine, m.p. 195°-198°, Rf =0.68 (methylene chloride:methanol=9.1).

Aufarbeitung

  1. temperatureat reflux for 12 hours
  2. temperatureAfter cooling to 0°
  3. filtrationfiltration
  4. washwashing with 2.0 liters of isopropanol and 3×400 ml of methanol
  5. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-b028616b7ef54bf2a3173957e652dd2f
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521184

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