Sodium Hydroxide → 2-Cyclopropyl-4-(4'-fluorophenyl)quinoline-3-carbonitrile

HRID 1760340Notes

Reaction equation

HRID 1760340 reaction equation
[CH:1]1([C:4](=O)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.CS(O)(=O)=O.[NH2:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:5]([C:6]#[N:7])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:16]3[C:15](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:14]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 98127633-Cyclopropyl-3-oxopropanenitrileHCID 53446970(2-Aminophenyl)(4-fluorophenyl)methanone methanesulfonate

Product 1

HCID 99657382-Cyclopropyl-4-(4'-fluorophenyl)quinoline-3-carbonitrileYield 98.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a glass flask having an internal volume of 50 mL, equipped with a stirring apparatus, a thermometer and a reflux condenser, 0.72 g (6.6 mmol) of 3-cyclopropyl-3-oxopropanenitrile, 1.92 g (6.0 mmol) of 2-amino-4′-fluorobenzophenone methanesulfonate having a purity of 97.3% and 10 mL of toluene were put in an atmosphere of nitrogen, and reaction was carried out at 80° C. for 2 hours. After completion of the reaction, the reaction liquid was cooled to room temperature, 7.0 mL (7.0 mmol) of a 1 mol/L sodium hydroxide aqueous solution was added thereto to make the reaction liquid basic, followed by liquid separation, and the obtained organic layer was analyzed by high performance liquid chromatography (absolute quantitative analysis), whereupon 1.70 g (yield: 98%) of 2-cyclopropyl-4-(4′-fluorophenyl)quinoline-3-carbonitrile was formed.

Workup

  1. customInto a glass flask having
  2. customan internal volume of 50 mL, equipped with a stirring apparatus
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. customthe reaction liquid basic
  6. customfollowed by liquid separation

Sources & evidence

ORD record
ord-b63d834995b648eabdd7b2bfac7d4e39
Source dataset
uspto-grants-2005_01
Patent number
US06841681B2

Reaction notes

Loading…