Ethanol → 3-Amino-4-[N-(4-cyanophenyl)amino]pyridine

HRID 892760

Reaktionsgleichung

Reaktionsgleichung von HRID 892760
O.O.[Sn](Cl)Cl.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2C=C[C:17]([NH2:20])=[C:16]([N+:21]([O-])=O)[CH2:15]2)=[CH:10][CH:9]=1)#[N:7].[CH2:24](O)[CH3:25]>Cl.O>[NH2:21][C:16]1[CH:17]=[N:20][CH:24]=[CH:25][C:15]=1[NH:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 19791284N-(4-cyanophenyl)-4-amino-3-nitropyridine

Produkt 1

HCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

According to a modification of the method of Pharm. Helv. Acta, 1975, 50, 188., tin dichloride dihydrate (56.4 g, 250 mmol) was added to a suspension of N-(4-cyanophenyl)-4-amino-3-nitropyridine (12.0 g, 50 mmol) in 2N aqueous hydrochloric acid (35 ml), water (150 ml) and ethanol (75 ml) and the resulting mixture was heated to reflux for 10 minutes under nitrogen. The mixture was cooled in ice, poured into ice-cold 2N aqueous sodium hydroxide (400 ml) and filtered. The creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water, and then dried in a vacuum desiccator. The product, 3-amino-4-(4'-cyanophenyl)aminopyridine, 9.31 g, gradually turns reddish brown on exposure to light and air.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 10 minutes under nitrogen
  3. temperatureThe mixture was cooled in ice
  4. filtrationfiltered
  5. washThe creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water
  6. customdried in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag
ord-11dad5c29e7e477a9b9c16962203c859
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05120747

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