Sodium hydride → 6-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridine

HRID 1699934Notes

Reaction equation

HRID 1699934 reaction equation
[C:1]([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Br:14])[N:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C)C=O>[Br:14][C:7]1[N:6]=[C:5]([N:4]([CH2:20][C:19]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:18]=2[Cl:17])[C:1](=[O:3])[CH3:2])[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 130420934-(Bromomethyl)-3-chlorobenzonitrileHCID 223878242-Acetamido-6-bromo-3-nitropyridine

Product 1

HCID 223878586-Bromo-2-(N-(2-chloro-4-cyanobenzyl)acetamido)-3-nitropyridineYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(Acetamido)-6-bromo-3-nitropyridine (3.21 g) was dissolved in dry N,N-dimethylformamide (16 ml), and sodium hydride (60% in oil, 326 mg) was added under ice-cooling. The mixture was stirred for 30 min. A solution of 2-chloro-4-cyanobenzyl bromide (2.34 g) in dry N,N-dimethylformamide (4 ml) was dropwise added at the same temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the objective compound (4.17 g) as a pale-yellow powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-586a7316283d4e5dbb54efcb3055df61
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

Loading…