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

HRID 1836294Notes

Reaction equation

HRID 1836294 reaction equation
C(=[N:14][CH:15]([CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1)[C:16]#[N:17])(C1C=CC=CC=1)C1C=CC=CC=1.Cl>O1CCOCC1>[NH2:14][CH:15]([CH2:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1)[C:16]#[N:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 234992122-(Benzhydrylideneamino)-3-quinolin-4-yl-propionitrile

Product 1

HCID 234991982-Amino-3-quinolin-4-yl-propionitrileYield 43%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-(Benzhydrylideneamino)-3-quinolin-4-yl-propionitrile (0.155 g, 4.29 mmol) in 5 ml dioxane, 1N HCl (1.3 ml, 12.8 mmol) was added and the reaction mixture stirred at room temperature overnight. The solution was concentrated under reduced pressure, partitioned between 10 ml water and EtOAc (10 ml). The organic layer was dried over sodium sulfate filtered and concentrated to give 2-Amino-3-quinolin-4-yl-propionitrile 0.036 g (43%) which was used as such for the subsequent step.

Workup

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

Sources & evidence

ORD record
ord-0555953eb73e48df8c62b4c2fa2b4345
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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