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Methyl iodide → 5-Chloro-1-methyl-3-nitropyridin-2-one

HRID 2410122
Notes
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Reaction equation

HRID 2410122 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[C:7]([OH:10])=[N:8][CH:9]=1.[CH3:14]I>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[C:7](=[O:10])[N:8]([CH3:14])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526657HCID 178526657, compound

Product 1

HCID 867031195-Chloro-1-methyl-3-nitropyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of NaH (577 mg, 14.4 mmol) and 5-chloro-2-hydroxy-3-nitropyridine (2.1 g, 12.0 mmol) in DMF (21 mL) was stirred for 1 h at 5° C. Methyl iodide (1.1 mL, 18.0 mmol) was added. The resulting mixture was allowed to warm to rt, stirred overnight, cooled to 0° C., quenched by addition of water, and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was used without further purification. tR: 0.61 min (LC-MS 2); ESI-MS: 189.1/191.1 [M+H]+ (LC-MS 2).

Workup

  1. temperatureto warm to rt
  2. stirringstirred overnight
  3. temperaturecooled to 0° C.
  4. customquenched by addition of water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was used without further purification

Sources & evidence

ORD record
ord-de86455240f14e0db4e69d55d7d77106
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815926B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes