Methyl iodide → 4H-Imidazo(4,5-c)(1,8)naphthyridin-4-one, 3,5-dihydro-3-methyl-5-phenyl-

HRID 1735162Notes

Reaction equation

HRID 1735162 reaction equation
[C:1]1([N:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[N:17]=[CH:18][NH:19][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[CH3:25]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:25][N:19]1[C:9]2[C:8](=[O:20])[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]=2[N:17]=[CH:18]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 126487KF 17625HCID 178418361HCID 178418361, compound

Product 1

HCID 30719594H-Imidazo(4,5-c)(1,8)naphthyridin-4-one, 3,5-dihydro-3-methyl-5-phenyl-Yield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of dimethylformamide was dissolved 0.80 g (3.1 mmol) of Compound 3 obtained in Example 3, and 0.18 g (4.6 mmol) of 60% sodium hydride in oil was added to the solution at room temperature. After evolution of hydrogen ceased, 0.40 ml (6.3 mmol) of methyl iodide was added to the reaction mixture, followed by stirring for 5 hours. Then, 2 ml of a saturated aqueous solution of ammonium chloride was added to the mixture, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (developing solvent: chloroform/methanol=70/1) to obtain crystals. Recrystallization from ethanol-isopropyl ether gave 0.61 g (yield 72%) of Compound 4 as colorless crystals.

Workup

  1. additionwas added to the solution at room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain crystals
  4. customRecrystallization from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-e8f2484bf3c44386ab624ee2a6d6658a
Source dataset
uspto-grants-1996_07
Patent number
US05536730

Reaction notes

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