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

HRID 1760342Notes

Reaction equation

HRID 1760342 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 91%

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, a reflux condenser and a Dean-Stark apparatus, 10.72 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 under at 110° C. for 2 hours while distilling off the formed water. 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 1.57 g (yield: 91%) 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. distillationwhile distilling off the formed water
  4. customAfter completion of the reaction
  5. customthe reaction liquid
  6. customthe reaction liquid basic
  7. customfollowed by liquid separation

Sources & evidence

ORD record
ord-6d7d89a32988436c84b63e25d2728170
Source dataset
uspto-grants-2005_01
Patent number
US06841681B2

Reaction notes

Loading…