1,4-Dioxane → HCID 21914017, compound

HRID 1008068Notes

Reaction equation

HRID 1008068 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[C:5]([CH3:17])=[C:4]([CH3:18])[N:3]=1.[O:19]1[CH2:24][CH2:23]OCC1>>[CH3:18][C:4]1[C:5]([CH3:17])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([O:19][C:24]2[CH:23]=[CH:6][CH:5]=[CH:4][CH:18]=2)[N:3]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 21913181HCID 21913181, compound

Product 1

HCID 21914017HCID 21914017, compound

Procedure

4-[(2-Chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butan-1-ol (20.00 g, 93.07 mmol) and additional dioxane (˜30 mL) were added. The reaction mixture was heated at reflux for 3 hours and then allowed to stand at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (200 mL) and then extracted with ethyl acetate (300 mL). The extract was washed with water (2×100 mL) then with brine, dried over magnesium sulfate, filtered and then concentrated under reduced pressure to provide an oil. The oil was purified by flash chromatography (600 mL of silica gel, eluting initially with 2000 mL 1:3 ethyl acetate:hexanes, then with 2000 mL 1:1 ethyl acetate:hexanes and finally with 1000 mL 3:1 ethyl acetate: hexanes) to provide 13.46 g of 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butan-1-ol as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with water (200 mL)
  5. extractionextracted with ethyl acetate (300 mL)
  6. washThe extract was washed with water (2×100 mL)
  7. dry with materialwith brine, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto provide an oil
  11. customThe oil was purified by flash chromatography (600 mL of silica gel
  12. washeluting initially with 2000 mL 1:3 ethyl acetate

Sources & evidence

ORD record
ord-db95ae0c32cc43dd9bf24eda189ac35d
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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