Water → N-Ethyl-5-nitro-2-phenoxypyridin-4-amine

HRID 1394226Notes

Reaction equation

HRID 1394226 reaction equation
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[C:10]1[CH:15]=[C:14]([NH:16][CH2:17][CH3:18])[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=1.O>C1COCC1>[CH2:17]([NH:16][C:14]1[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=[C:10]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4445035Phenolate SodiumHCID 591770742-chloro-N-ethyl-5-nitropyridin-4-amine

Product 1

HCID 69158825N-Ethyl-5-nitro-2-phenoxypyridin-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium phenoxide (prepared from phenol and NaH) (6 mmol) in THF (3 mL) was added to a solution of the product from Step 1 (600 mg, 3.0 mmol) in THF (2 mL) and the resulting solution was heated to reflux overnight. The solution was cooled, poured into H2O and extracted with EtOAc. The organic layers were washed with H2O and brine, dried, filtered and concentrated to give a residue which was purified by column chromatography (5-80% EtOAc in hex) to give the title compound which was used directly in the next step. MS (ES+) m/e 260. [M+H]+.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux overnight
  3. temperatureThe solution was cooled
  4. extractionextracted with EtOAc
  5. washThe organic layers were washed with H2O and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue which
  10. customwas purified by column chromatography (5-80% EtOAc in hex)

Sources & evidence

ORD record
ord-87bd748d923a4686aee3c7b7ee89e09e
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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