2-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile → 2-Amino-3-quinolin-4-yl-butyronitrile

HRID 1836298Notes

Reaction equation

HRID 1836298 reaction equation
C(=[N:14][CH:15]([CH:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1)[CH3:19])[C:16]#[N:17])(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.Cl>[NH2:14][CH:15]([CH:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1)[CH3:19])[C:16]#[N:17]

Participants

4

Reactant 1

HCID 234992012-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile

Product 1

HCID 234991682-Amino-3-quinolin-4-yl-butyronitrileYield 102.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To 2-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile (3.0 g, 7.3 mmol) in 30 ml dioxane, 1N HCl (30 ml, 29.99 mmol, was added and the reaction mixture stirred at room temperature overnight. The solution was then concentrated under reduced pressure, partitioned between water (10 ml) and EtOAc (10 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to give 1.58 g (88%) of the product which was used as such for the subsequent step.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. custompartitioned between water (10 ml) and EtOAc (10 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-596929d7cb1c4815aaf9c9c6c807ca4f
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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