Water → 6-(2,2-Difluoroethoxy)-5-methyl-3-nitro-2-pyridineamine

HRID 505389Notes

Reaction equation

HRID 505389 reaction equation
[F:1][CH:2]([F:5])[CH2:3][OH:4].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:10]=1[CH3:19].O>O1CCCC1>[F:1][CH:2]([F:5])[CH2:3][O:4][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:10]=1[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1361872,2-Difluoroethan-1-olHCID 218373796-Chloro-5-methyl-3-nitropyridin-2-amine

Product 1

HCID 594298356-(2,2-Difluoroethoxy)-5-methyl-3-nitro-2-pyridineamineYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,2-Difluoro ethanol (418 mg, 5.1 mmol) was dissolved in tetrahydrofuran (15 ml), sodium hydride (60%) (180 mg, 4.5 mmol) was added thereto under nitrogen atmosphere, and the reaction mixture was stirred for 30 minutes at room temperature. A solution of 6-chloro-5-methyl-3-nitro-2-pyridineamine (600 mg, 3.20 mmol) in tetrahydrofuran (15 ml) was dropped, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution and extracted with ethyl acetate, and after washed with sodium bicarbonate solution, dried over magnesium sulfate. The residue obtained by evaporating the solvent was triturated with n-hexane to yield the title compound (685 mg, 3.1 mmol, 96%) as an orange solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washafter washed with sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe residue obtained
  6. customby evaporating the solvent
  7. customwas triturated with n-hexane

Sources & evidence

ORD record
ord-19999b7d6a9a4f779d3e4170838ef18b
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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