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1,10-Phenanthroline → N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

HRID 655867
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 655867
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1.[C:30]([O:34][C:35]([NH:37][NH2:38])=[O:36])([CH3:33])([CH3:32])[CH3:31]>[Cu](I)I.CN(C=O)C>[C:30]([O:34][C:35]([N:37]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)[NH2:38])=[O:36])([CH3:33])([CH3:32])[CH3:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 764674-Iodobenzonitrile

Produkt 1

HCID 11230036N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl EsterAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717
Copper iodide
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Copper iodide (18 mg, 0.05 eq, 0.09 mmol), 1,10-phenanthroline (67 mg, 0.2 eq, 0.37 mmol) and caesium carbonate (0.84 g, 1.4 eq, 2.6 mmol) were mixed in a RB flask, placed under vacuum and purged with N2 (g). 4-iodo-benzonitrile (0.5 g, 1.0 eq, 1.85 mmol), hydrazine carboxylic acid tert-butyl ester (0.3 g, 1.2 eq, 2.22 mmol) and DMF (25 ml) were added to the mixture which was then heated to 80° C. with stirring under an inert atmosphere for 16 hours. The reaction mixture was allowed to cool and the solvent was removed in vacuo. The resultant residue was absorbed onto silica and purified by column chromatography using heptane/ethyl acetate (7:3) as eluent to yield the title compound as a pale orange solid (0.23 g, 1.0 mmol, 45%). LCMS: [M+H]+=234, rt=1.94 min, 97% purity.

Aufarbeitung

  1. custompurged with N2 (g)
  2. temperatureto cool
  3. customthe solvent was removed in vacuo
  4. customThe resultant residue was absorbed onto silica
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f9b04c8b2db244ebbe6aefc2242c4bde
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071607B2

Notizen zur Reaktion

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