Pivalic acid → 2-(tert-Butyl)isonicotinonitrile

HRID 1181387

Reaktionsgleichung

Reaktionsgleichung von HRID 1181387
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].[CH3:9][C:10](C)([CH3:14])[C:11](O)=O.[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O>S(=O)(=O)(O)O.O.[N+]([O-])([O-])=O.[Ag+]>[C:10]([C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][N:6]=1)([CH3:14])([CH3:11])[CH3:9]

Komponenten

7

Edukt 3

HCID 6417Pivalic acidHCID 75064-CyanopyridineHCID 62648Ammonium Persulfate

Produkt 1

HCID 6933222-(tert-Butyl)isonicotinonitrileAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A mixture of 4-cyanopyridine (10 g, 96 mmol), trimethylacetic acid (9.8 g, 96 mmol), and silver nitrate (1.63 g, 9.6 mmol) in 10% aqueous sulfuric acid (100 ml) at 70° C. was treated with a solution of ammonium peroxodisulfate (21.9 g, 96 mmol) in water (120 ml) according to the method of Description 10. Purification by column chromatography on silica eluting with 10% Et2O in iso-hexanes gave the title compound (6.5 g, 42%).

Aufarbeitung

  1. customPurification by column chromatography on silica eluting with 10% Et2O in iso-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7ba1e8b2858940a5a20c6df8d7312dd5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285563B2

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