Ammonia → 1-(Quinolin-6-YL)ethanamine

HRID 16025Notes

Reaction equation

HRID 16025 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](=[N:13]O)[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CO.N.[H][H]>CCO.[Ni]>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([NH2:13])[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 722593651-Quinolin-6-yl-ethanone oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 208428591-(Quinolin-6-YL)ethanamineYield 97.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-quinolin-6-yl-ethanone oxime (4.54 g, 24.4 mmol) in EtOH (50 mL) was added methanol solution of NH3 (7N, 12 mL, 80 mmol). A slurry of Raney Nickel (washed 3× with EtOH) about 2 g was added followed by a hydrogen-filled balloon. The reaction was stirred at ambient temperature for 16 hours under hydrogen-filled balloon. The reaction mixture was filtered over a pad of celite and the mother liquor was concentrated to give quantitative 1-quinolin-6-yl-ethylamine (4.1 g).

Workup

  1. additionfilled balloon
  2. additionfilled balloon
  3. filtrationThe reaction mixture was filtered over a pad of celite
  4. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-084b8cd3fa234f8b84ed56a66590eed5
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Reaction notes

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