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

HRID 1519791Notes

Reaction equation

HRID 1519791 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-e16928ab0dc848c683f553fd742e40a1
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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