Ammonia → (2,2-dimethyl-2H-chromen-6-yl)methanamine

HRID 911278

Reaktionsgleichung

[CH3:1][C:2]1([CH3:14])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[O:3]1.C(O)C.N>CO.[Ni]>[NH2:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:14])([CH3:1])[CH:11]=[CH:10]2

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Add 2,2-dimethyl-2H-chromene-6-carbonitrile (1.5 g, 8.1 mmol) and ethanol wet Raney® activated nickel (0.4 g) to a Parr pressure vessel. Immediately add 7N ammonia in methanol (170 mL) and seal the vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (3400 KPa), seal the vessel, agitate the reaction and heat to 60° C. for 20 h. Turn off the heat and allow the reaction mixture to cool to ambient temperature. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the Raney® nickel. Purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1) to obtain the title compound (1.5 g, 97%). MS (ES+) m/z: 175 M+H−NH3)+.

Aufarbeitung

customPurge the reaction vessel with nitrogen
customseal the vessel
customthe reaction
temperatureheat
temperatureto cool to ambient temperature
customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
filtrationFilter the reaction mixture
customto remove the Raney® nickel
customPurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1)

Quellen und Nachweise

ORD-Eintrag: ord-6c5c2c4d22d44ba9b728fce81a9e5bda
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08022062B2

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