Sodium Hydroxide → (2-Chloro-6-methoxyquinolin-4-yl)acetonitrile

HRID 725885Notes

Reaction equation

HRID 725885 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]=[CH:13][N:14](C)C)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:17][CH3:18])[CH:8]=2)[N:3]=1.NOS(O)(=O)=O.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]#[N:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:17][CH3:18])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 53676043[2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamine

Product 1

HCID 19709968(2-Chloro-6-methoxyquinolin-4-yl)acetonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[2-(2-Chloro-6-methoxyquinolin-4-yl)ethenyl]dimethylamine (28.3 g, 0.11 mol) and hydroxylamine-O-sulfonic acid (40.2 g, 0.36 mol) were suspended in water (1.2 L), and the mixture was stirred at room temperature for 70 hours. The reaction mixture was neutralized with an aqueous solution of sodium hydroxide, and the organic materials were extracted with a mixed solvent of 5% methanol/ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to obtain the title compound (19.9 g, 79%).

Workup

  1. extractionthe organic materials were extracted with a mixed solvent of 5% methanol/ethyl acetate
  2. washThe extract was washed with saturated brine and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e10ac0d15e094f8584b26034059822ed
Source dataset
uspto-grants-1998_01
Patent number
US05708005

Reaction notes

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