Methanol → 2-Methoxypyridin-4-amine

HRID 272703

Reaction equation

HRID 272703 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][OH:10]>>[CH3:9][O:10][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 844322-Chloropyridin-4-amine

Product 1

HCID 2808912-Methoxypyridin-4-amine

Procedure

Na (0.7 g, 30 mmol) was added to methanol (10 mL) at room temperature. Once all Na had dissolved, 2-chloro-4-aminopyridine (0.5 g, 3.9 mmol) was added. The solution was heated to reflux for 16 hours. After the reaction solution cooled to room, it was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with additional ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to give the title product. MS (DCI) m/e 125 (M+H)+.

Workup

  1. dissolutionOnce all Na had dissolved
  2. temperatureThe solution was heated
  3. temperatureto reflux for 16 hours
  4. temperatureAfter the reaction solution cooled to room, it
  5. customwas partitioned between ethyl acetate and water
  6. extractionThe aqueous layer was extracted twice with additional ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-85070f94ff054c27998d8d260804425f
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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