HCID 19709759, Verbindung → 4-(4-methyl-1H-imidazol-1-yl)-2-aminomethylaniline

HRID 472154

Reaktionsgleichung

Reaktionsgleichung von HRID 472154
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([C:14]#[N:15])[CH:8]=2)[CH:6]=1.[H][H]>N.CO.[Ni+2]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH2:14][NH2:15])[CH:8]=2)[CH:6]=1

Komponenten

5

Edukt 2

HCID 19709759HCID 19709759, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 582704594-(4-methyl-1H-imidazol-1-yl)-2-aminomethylanilineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 934Nickel cationKatalysatorHCID 21705897Ammonia methanolLösungsmittel

Versuchsvorschrift

To 4-(4-methyl-1H-imidazol-1-yl)-2-cyanoaniline (15.5 g; 78.2 mmol) dissolved in 10% NH3/methanol was added Raney-Nichel (5 g), the resulting mixture was hydrogenated at 60° C., at an hydrogen pressure of 60 bar, for 24 hours. The nitrogen purged reaction mixture was filtered on celite, the cake was washed with methanol and the combined filtrate and washings evaporated. The residue was purified by column chromatography over silica gel (DCM/MeOH/2M NH3, 85:10:5) evaporation of the combined appropriate fractions afforded the pure titled product as yellow-orange solid (12.9 g, 82%). C11H14N4, MW: 202.26; 1H-NMR (300 MHz, d6-DMSO) ppm: 2.13 (s, 3H), 5.24 (s, 2H), 6.67 (d, 1H), 7.08 (dd, 1H), 7.17 (t, 1H), 7.23 (d, 1H), 7.81 (d, 1H).

Aufarbeitung

  1. customThe nitrogen purged
  2. customreaction mixture
  3. filtrationwas filtered on celite
  4. washthe cake was washed with methanol
  5. customthe combined filtrate and washings evaporated
  6. customThe residue was purified by column chromatography over silica gel (DCM/MeOH/2M NH3, 85:10:5) evaporation of the combined appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-36d3c6d611b8452b9e71b29f7cdebd38
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633208B2

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