Ammonia → 2-(Acetamido)-6-(2-aminoethyl)quinoline

反応式

[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][C:16]#[N:17])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].N.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CCO.[Ni]>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][CH2:16][NH2:17])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

参加物

実験手順

Compound 47 (0.060 g, 0.266 mmol) was diluted in absolute EtOH (7 mL) and methanolic ammonia (7 N, 7 mL) was added. Raney nickel (˜1.5 g, washed with H2O and MeOH) was added, and the mixture was degassed and hydrogenated with a balloon at room temperature for 30 min while stirring rapidly. The clear solution was decanted away from the nickel and was filtered through a Pall 0.2 μm syringe filter to remove fine particulate matter. The solution was concentrated and dried in vacuo to yield a colorless gum that became a white semisolid upon standing (0.050 g, 82%). Conversion to this amine was confirmed by 1H NMR spectrometry, TLC, MS, and ninhydrin staining, and it was used crude without any further characterization or purification.