Hydrochloric Acid → 5-Bromo-3-morpholinopyridin-2-ol

HRID 594039Notes

Reaction equation

HRID 594039 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:5]([O:8]C)=[N:6][CH:7]=1.Cl>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:5](=[O:8])[NH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 904090924-(5-Bromo-2-methoxypyridin-3-yl)morpholine

Product 1

HCID 904098535-Bromo-3-morpholinopyridin-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(5-bromo-2-methoxypyridin-3-yl)morpholine (1.0 equiv.) in 1,4-dioxane (0.3 M) was added concentrated HCl (5 equiv.) and the solution was heated to 100° C. for 1 h. Upon cooling to room temperature, the solution was concentrated to dryness under vacuo, then dissolved in water and neutralized with solid sodium bicarbonate. The precipitate was filtered, washed with water and dried under vacuo to give 5-bromo-3-morpholinopyridin-2(1H)-one as a beige solid in 93% yield. LCMS m/z (M+H)=258.9/260.9, Rt=0.48 min.

Workup

  1. temperatureUpon cooling to room temperature
  2. concentrationthe solution was concentrated to dryness under vacuo
  3. dissolutiondissolved in water and neutralized with solid sodium bicarbonate
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried under vacuo

Sources & evidence

ORD record
ord-c7c0573354f94c41b214776f9f52d15f
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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