Water → HCID 67061179, compound

HRID 598405Notes

Reaction equation

HRID 598405 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][NH:13][C:12](=[O:19])[CH:11]=1.[H-].[Na+].[CH3:22]I.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]([CH3:22])[C:12](=[O:19])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57438270HCID 57438270, compound

Product 1

HCID 67061179HCID 67061179, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(2-Fluoro-4-iodophenylamino)-5-nitropyridin-2(1H)-one (1.28 g, 3.41 mmol) was dissolved in dry DMF (20 mL) and cooled to 0° C. under an ice-bath. To the solution was added NaH (60% in oil) (168 mg, 4.2 mmol) portion-wise. The resulted mixture was stirred at 0° C. for 1 hour, followed by the addition of methyl iodide (260 uL, 4.17 mmol) drop-wise through a syringe. The solution was allowed to warm to room temperature and stirred for 16 hours. Water (20 mL) was added slowly and stirring was continued for 30 minutes. The resulted yellow precipitate was filtered, dried under vacuum at 40° C. for 5 hours, and used for the next reaction without further purification. (1.017 g, 77% yield)

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. stirringstirring
  4. waitwas continued for 30 minutes
  5. filtrationThe resulted yellow precipitate was filtered
  6. customdried under vacuum at 40° C. for 5 hours
  7. customused for the next reaction without further purification

Sources & evidence

ORD record
ord-96f34065de1f44698d53c8ef9ba892a7
Source dataset
uspto-grants-2011_03
Patent number
US07897624B2

Reaction notes

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