Water → Methyl 4-Hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 1179296Notes

Reaction equation

HRID 1179296 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6](=[O:21])[CH2:7][C:8]([NH:10][C:11]1[C:12]([C:17]([O:19]C)=O)=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:9].O>C1COCC1>[OH:19][C:17]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][N:13]=2)[NH:10][C:8](=[O:9])[C:7]=1[C:6]([O:5][CH3:4])=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 42637833Methyl 3-[(3-methoxy-3-oxopropanoyl)amino]pyridine-2-carboxylate

Product 1

HCID 54729994Methyl 4-Hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (0.73 g, 13.5 mmol) was added to 2 methyl 3-[(3-methoxy-3-oxopropanoyl)amino]pyridine-2-carboxylate (0.9 g, 3.4 mmol) dissolved in THF (20 mL). The reaction was stirred overnight. Water was added and the solvents removed. The residue was dissolved in water and purified by reverse phase HPLC eluting with a gradient of 5-40% acetonitrile/water (0.1% TFA) to give the product as a yellow solid.

Workup

  1. customthe solvents removed
  2. dissolutionThe residue was dissolved in water
  3. custompurified by reverse phase HPLC
  4. washeluting with a gradient of 5-40% acetonitrile/water (0.1% TFA)

Sources & evidence

ORD record
ord-ce6430c383cc4bed966ac9a3a034aa0e
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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