3-(Cyanomethyl)pyridine-2-carbonitrile → 6-Amino-8-benzyl-1,7-naphthyridine

HRID 369028

Reaktionsgleichung

Reaktionsgleichung von HRID 369028
[C:1]([C:3]1[C:8]([CH2:9][C:10]#[N:11])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[CH2:12]([Mg]Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1.O1CCCC1>[NH2:11][C:10]1[CH:9]=[C:8]2[C:3](=[C:1]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:2]=1)[N:4]=[CH:5][CH:6]=[CH:7]2

Komponenten

5

Edukt 2

HCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileHCID 178419663HCID 178419663, Verbindung

Produkt 1

HCID 232846456-Amino-8-benzyl-1,7-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-cyano-3-pyridylacetonitrile (2 g, 0.014 mol) in toluene (20 ml) is added benzylmagnesium bromide 8.4 ml, 2N in tetrahydrofuran, 0.17 mol) at ambient temperature. After 1 h the reaction is quenched with a saturated solution of ammonium chloride. The product is extracted with ethyl acetate and the organic layer washed with 2N NaOH and water. The product is purified by flash column chromatography on silica gel (10:3 toluene/acetone) affording the title compound. Mass M+H 236; mp 113-116° C.

Aufarbeitung

  1. customAfter 1 h the reaction is quenched with a saturated solution of ammonium chloride
  2. extractionThe product is extracted with ethyl acetate
  3. washthe organic layer washed with 2N NaOH and water
  4. customThe product is purified by flash column chromatography on silica gel (10:3 toluene/acetone)

Quellen und Nachweise

ORD-Eintrag
ord-8b5b8840371746999baa1b1e3589ae07
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136821

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