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

HRID 1179324Notes

Reaction equation

HRID 1179324 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]([NH:7][C:8]1[C:9]([C:14]([O:16]C)=O)=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:6].C[O-].[Na+]>>[OH:16][C:14]1[C:9]2[C:8](=[CH:13][CH:12]=[CH:11][N:10]=2)[NH:7][C:5](=[O:6])[C:4]=1[C:3]([O:2][CH3:1])=[O:18]

Participants

3

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 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

Procedure

To a solution of methyl 3-[(3-methoxy-3-oxopropanoyl)amino]pyridine-2-carboxylate (7.3 g, 29.9 mmol, prepared as described in example 1) in anhydrous TBF (100 mL) was added solid sodium methoxide (3.9 g, 72.4 mmol) at 0° C. Immediately following the addition of the sodium methoxide, solids crashed out of the solution. The ice bath was then removed and the suspension was stirred for an additional 0.5 hours. The suspension was then filtered through a medium porosity filtration funnel to afford yellow solids.

Workup

  1. customThe ice bath was then removed
  2. filtrationThe suspension was then filtered through a medium porosity filtration funnel
  3. customto afford yellow solids

Sources & evidence

ORD record
ord-f10dd82cdede403fb719c0f1b365ec62
Source dataset
uspto-grants-2007_10
Patent number
US07279487B2

Reaction notes

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