Methyl iodide → HCID 10444119, compound

HRID 638216Notes

Reaction equation

HRID 638216 reaction equation
[C:1]1([C:7]2[N:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][C:11](=[O:17])[NH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[CH3:18][N:12]1[C:13]2[C:8](=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:16]=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]1=[O:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10104952HCID 10104952, compound

Product 1

HCID 10444119HCID 10444119, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 22.2 g of 5-phenyl-1,6-naphthyridin-2(1H)-one, 13.18 g of anhydrous potassium carbonate and 300 ml of dimethylformamide was heated with stirring on a steam bath for 1 hour and to this mixture was added 6.9 g of methyl iodide. The resultig mixture was heated with stirring for an additional 6 hours, allowed to cool and the solvent removed by distillation under reduced pressure. To the residue was added 100 ml of 20% acetic acid and the resulting pale yellow solid was collected, washed with water, dried, recrystallized from methanol and dried at 90° C. to yield 16.4 g of 1-methyl-5-phenyl-1,6-naphthyridin-2(1H)-one, m.p. 190°-192° C.

Workup

  1. temperaturewas heated
  2. temperatureThe resultig mixture was heated
  3. stirringwith stirring for an additional 6 hours
  4. temperatureto cool
  5. customthe solvent removed by distillation under reduced pressure
  6. additionTo the residue was added 100 ml of 20% acetic acid
  7. customthe resulting pale yellow solid was collected
  8. washwashed with water
  9. customdried
  10. customrecrystallized from methanol
  11. customdried at 90° C.

Sources & evidence

ORD record
ord-d04e2a24c7c84ec5b91945d7a6e5da12
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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