Sodium percarbonate → 4-(4-Fluorophenyl)-7-methylquinoline-2-carboxamide

HRID 922751Notes

Reaction equation

HRID 922751 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[C:10]([C:19]#[N:20])[CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:22].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>CC(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[C:10]([C:19]([NH2:20])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159762Sodium percarbonateHCID 574378434-(4-Fluorophenyl)-7-methyl-2-quinolinecarbonitrile

Product 1

HCID 895439014-(4-Fluorophenyl)-7-methylquinoline-2-carboxamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

4-(4-Fluorophenyl)-7-methylquinoline-2-carbonitrile (1-6, 25 mg, 0.095 mmol, 1.0 equiv.) was dissolved in acetone (2.3 mL)/water (1.5 mL) and sodium percarbonate (79.0 mg, 0.477 mmol, 5.0 equiv) was added. The resulting mixture was stirred at 50° C. for 1 hour. The mixture was cooled and concentrated. The crude residue was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier). Fractions containing product were pooled and treated with Na2CO3. The resulting mixture was extracted with CHCl3. The combined organic layers were dried (MgSO4), filtered, and concentrated to afford 4-(4-fluorophenyl)-7-methylquinoline-2-carboxamide (1-7). LRMS m/z (M+H)+ 280.9 found, 281.3 required.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customThe crude residue was purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA modifier)
  5. additionFractions containing product
  6. additiontreated with Na2CO3
  7. extractionThe resulting mixture was extracted with CHCl3
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d5c240bb10634b8aa948fd0a1ceb5c9e
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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