Acetonitrile → 4-phenylquinolin-2-amine

HRID 432126Notes

Reaction equation

HRID 432126 reaction equation
[OH-].[K+].[NH2:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=O.[C:18](#[N:20])[CH3:19]>>[C:8]1([C:6]2[C:5]3[C:4](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:3]=[C:18]([NH2:20])[CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 14797Potassium HydroxideHCID 760802-Aminobenzophenone

Product 1

HCID 6722654-phenylquinolin-2-amine

Procedure

Acetonitrile (150 mL) was heated to reflux for 30 minutes in the presence of potassium hydroxide (14.2 g, 254 mmol). 2-amino-benzophenone (10.0 g, 50.7 mmol) in acetonitrile (165 mL) was added to the reaction mixture. After heating to reflux overnight, the mixture was cooled to room temperature, and the resulting solid was filtered. HCl (1.0 M, 100 mL) was added to the solution, and the resulting solid was filtered. The solids were combined, dissolved in ethyl acetate, dried over magnesium sulfate, and filtered. The volatile components were removed with a rotary evaporator, and the solid was recrystallized from ethyl acetate and heptane.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux overnight
  3. filtrationthe resulting solid was filtered
  4. additionHCl (1.0 M, 100 mL) was added to the solution
  5. filtrationthe resulting solid was filtered
  6. dissolutiondissolved in ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe volatile components were removed with a rotary evaporator
  10. customthe solid was recrystallized from ethyl acetate and heptane

Sources & evidence

ORD record
ord-7e52a33688144b61ba511d8fa390bcbb
Source dataset
uspto-grants-2003_12
Patent number
US06661023B2

Reaction notes

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