Methyl iodide → HCID 58093678, compound

HRID 1034947Notes

Reaction equation

HRID 1034947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[N:11]=1)[C:8](=[O:13])[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH3:16]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[N:11]=1)[C:8](=[O:13])[N:7]([CH3:16])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 580937976,8-Dichloro-2,7-naphthyridin-1(2H)-one

Product 1

HCID 58093678HCID 58093678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6,8-dichloro-2,7-naphthyridin-1(2H)-one (215.0 mg, 1.0 mmol) in dry DMF (10 mL) was added NaH (100 mg, 60% in mineral oil, 2.5 mmol) at 0° C. under N2. After the reaction mixture was allowed to be warmed to room temperature and stirred for 20 minutes, CH3I (0.25 mL, 568.08 mg, 4.0 mmol) was added via syringe. The reaction mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL), washed with saturated NH4Cl solution (2×50 mL), water (30 mL) and brine (20 mL), and concentrated to afford the crude title compound. ESI-MS m/z 229.0 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (100 mL)
  4. washwashed with saturated NH4Cl solution (2×50 mL), water (30 mL) and brine (20 mL)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-003aafac274342cfb82118382536f0d0
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Reaction notes

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