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

HRID 1503156Notes

Reaction equation

HRID 1503156 reaction equation
[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]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10236NinhydrinHCID 1182521902-(Acetamido)-6-(cyanomethyl)quinoline

Product 1

HCID 1182521832-(Acetamido)-6-(2-aminoethyl)quinoline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  1. customthe mixture was degassed
  2. customThe clear solution was decanted away from the nickel
  3. filtrationwas filtered through a Pall 0.2 μm syringe
  4. filtrationfilter
  5. customto remove fine particulate matter
  6. concentrationThe solution was concentrated
  7. customdried in vacuo
  8. customto yield a colorless gum that
  9. customwithout any further characterization or purification

Sources & evidence

ORD record
ord-e227a6b8e231457492184a031fe6837e
Source dataset
uspto-grants-2015_12
Patent number
US09212144B2

Reaction notes

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