Sodium Hydroxide → 2-(2-oxo-1,6-naphthyridin-1(2H)-yl)acetic acid

HRID 2098003Notes

Reaction equation

HRID 2098003 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]1[CH2:12][C:13]([O:15]C)=[O:14].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]1[CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68784941methyl 2-(2-oxo-1,6-naphthyridin-1(2H)-yl)acetate

Product 1

HCID 687852582-(2-oxo-1,6-naphthyridin-1(2H)-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(2-oxo-1,6-naphthyridin-1(2H)-yl)acetate (1.51 g, 6.92 mmol) in THF (10 mL) was added sodium hydroxide (4 mL of a 3 N aqueous solution, 13.8 mmol) and the reaction mixture was stirred at room temperature for 18 h. The resulting solution was diluted with ethyl acetate and washed with water. The aqueous phase was separated, adjusted to pH 2 with aqueous HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), filtered and concentrated under vacuum to give 2-(2-oxo-1,6-naphthyridin-1(2H)-yl)acetic acid. Retention time (min)=0.368, method [3], MS (ESI) 205.0 (M+H).

Workup

  1. washwashed with water
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ad4138c3d8fb4f33b76359ab8820c3b6
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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