Hydrochloric Acid → 2-Amino-3-quinolin-4-yl-butyronitrile

HRID 1597366Notes

Reaction equation

HRID 1597366 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.Cl>O1CCOCC1>[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 2

HCID 313Hydrochloric AcidHCID 234992012-(Benzhydrylideneamino)-3-quinolin-4-yl-butyronitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 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-8fbb9ce76cff434b95ef0160400455f1
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

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