2-Chloro-5-nitropyridine → HCID 86657964, compound

HRID 2366762Notes

Reaction equation

HRID 2366762 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][CH3:13])[CH:7]=1)=[O:4].Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]([F:14])([F:15])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([CH3:13])[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=2)[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 783082-Chloro-5-nitropyridineHCID 516892Sodium BicarbonateHCID 86657962HCID 86657962, compound

Product 1

HCID 86657964HCID 86657964, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2,2,2-trifluoro-N-[3-(methylamino)phenyl]acetamide (10.0 g, 45.8 mmol) in N,N-dimethylformamide (40 mL) was added 2-chloro-5-nitropyridine (7.99 g, 50.4 mmol), and the mixture was stirred at 120° C. for 23 hr. The reaction mixture was cooled to room temperature, aqueous sodium hydrogen carbonate solution (100 mL) was added, and the mixture was extracted with ethyl acetate (300 mL). The organic layer was washed with water (70 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The dried organic layer was purified by silica gel column chromatography (150 g, ethyl acetate) to give the title compound (15.0 g, 96%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (300 mL)
  3. washThe organic layer was washed with water (70 mL) and saturated brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe dried organic layer was purified by silica gel column chromatography (150 g, ethyl acetate)

Sources & evidence

ORD record
ord-8c72872c40084f89ad7d7801c737e636
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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