2-Amino-3-quinolin-4-yl-butyronitrile → 3-Quinolin-4-yl-butane-1,2-diamine

HRID 1597367Notes

Reaction equation

HRID 1597367 reaction equation
[NH2:1][CH:2]([CH:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)[CH3:6])[C:3]#[N:4]>C(O)C.N.[Ni]>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH:5]([CH3:6])[CH:2]([NH2:1])[CH2:3][NH2:4])=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 234991682-Amino-3-quinolin-4-yl-butyronitrile

Product 1

HCID 234991713-Quinolin-4-yl-butane-1,2-diamineYield 111.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

To 2-Amino-3-quinolin-4-yl-butyronitrile (1.58 g, 6.42 mmol) in 10 ml of ethanol, ammonia gas was bubbled for 15 minutes. 2 g of Raney Ni (washed with 2×50 ml water and 2×50 ml ethanol) was added to the solution and the reaction mixture was hydrogenated at 50 psi for 2 hours, filtered over celite and concentrated to give 1.54 g (96%) of the product which was then used as such for the subsequent step.

Workup

  1. filtrationfiltered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-19cdb0f92d79488cb15673a145eef816
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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