Dimethylformamide → HCID 22442122, compound

HRID 1972166Notes

Reaction equation

HRID 1972166 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[C:10]([CH3:15])=[N:11][CH:12]=[CH:13][CH:14]=1.[Cl:16][C:17]1[CH:22]=[C:21]([N+]([O-])=O)[CH:20]=[CH:19][N:18]=1>O>[Cl:16][C:17]1[CH:22]=[C:21]([O:8][C:9]2[C:10]([CH3:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 707192-Methylpyridin-3-olHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 22442122HCID 22442122, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (1.07 g, 42.3 mmol) was added to DMF (25 mL). 3-Hydroxy-2-methylpyridine (4.40 g, 40.3 mmol) was slowly added to the mixture and the reaction was stirred for 1 hour. 2-Chloro-4-nitropyridine (6.71 g, 42.3 mmol) was added and the reaction was stirred overnight at ambient temperature. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated to give the title compound (8.0 g, 90% yield) as a yellow oil, which solidified upon standing at ambient temperature.

Workup

  1. stirringthe reaction was stirred overnight at ambient temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4809731b9e334f94baf0eff92b975cf9
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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