Sodium Cyanide → 2-Oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

HRID 1521650Notes

Reaction equation

HRID 1521650 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[C-:13]#[N:14].[Na+]>CN1CCCC1=O.O.[Ni](Br)Br>[O:12]=[C:6]1[CH2:5][CH2:4][C:3]2[C:2]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][C:8]=2[NH:7]1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 665969262-Oxo-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 278492Nickel(II) bromideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of 5-chloro-3,4-dihydroquinolin-2(1H)-one (143-4; 1.8 g, 0.0099 mol) and nickel bromide (2.15 g, 0.0099 mol) in N-methyl-2-pyrrolidone (10 mL) was added sodium cyanide (0.97 g, 0.0198 mol) portion wise at room temperature. Reaction mixture was heated at 200° C. for 10 min under microwave irradiation. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. MS (M−1): 171.2.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3d4428a24cfa436f8d6162aacafb0694
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

Loading…