Water → HCID 21912946, compound

HRID 1008044Notes

Reaction equation

HRID 1008044 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]([O:17][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23](Cl)[C:22]=1[N+:29]([O-:31])=[O:30])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>COCCOCCOC.C(OCC)(=O)C>[CH2:10]([O:17][CH2:18][CH2:19][NH:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:22]=1[N+:29]([O-:31])=[O:30])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 21913088[2-(Benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine

Product 1

HCID 21912946HCID 21912946, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8150DiglymeSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, diglyme (20 mL) was added to sodium hydride (0.548 g, 13.7 mmol), which is available as a 60% dispersion in mineral oil, and the mixture was cooled to 0° C. A solution of phenol (1.35 g, 14.4 mmol) in diglyme (20 mL) was added, and the addition flask was rinsed with additional diglyme (2×5 mL), which was added to the reaction flask. The reaction became homogeneous and was stirred for 30 minutes. Solid [2-(benzyloxy)ethyl]-(2-chloro-6-methyl-3-nitropyridin-4-yl)amine (4.2 g, 13 mmol) was added, and the resulting dark solution was heated at 60° C. for 90 minutes. The reaction was allowed to cool and then slowly poured into water (500 mL) and stirred rapidly for 90 minutes. A yellow solid formed, which was isolated by filtration and dissolved in ethyl acetate. The solution was then dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a yellow oil, which began to crystallize over three days. The product was triturated with hexane, and the resulting solid was isolated by filtration and dried for two hours under high vacuum at 55° C. to provide 4.44 g of [2-(benzyloxy)ethyl]-(6-methyl-3-nitro-2-phenoxy-pyridin-4-yl)amine as a yellow solid.

Workup

  1. washthe addition flask was rinsed with additional diglyme (2×5 mL), which
  2. additionwas added to the reaction flask
  3. temperaturethe resulting dark solution was heated at 60° C. for 90 minutes
  4. temperatureto cool
  5. stirringstirred rapidly for 90 minutes
  6. customA yellow solid formed
  7. customwhich was isolated by filtration
  8. dry with materialThe solution was then dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto provide a yellow oil, which
  12. customto crystallize over three days
  13. customThe product was triturated with hexane
  14. customthe resulting solid was isolated by filtration
  15. customdried for two hours under high vacuum at 55° C.

Sources & evidence

ORD record
ord-26e665f5c1f94f6a8e2ed79e0cd66a56
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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