Water → Ethyl 1-benzyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 2194517Notes

Reaction equation

HRID 2194517 reaction equation
[O:1]=[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C)C=O>[CH2:23]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1=[O:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11564777Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

Product 1

HCID 67010119Ethyl 1-benzyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.50 g (6.9 mmol) of ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in N,N-dimethylformamide (30 mL), and 1.43 g (10.4 mmol) of potassium carbonate and 1.36 g (7.9 mmol) of benzyl bromide were added thereto. The resulting mixture was stirred for one whole day and night at room temperature. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The organic phase was dried, filtered, and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=3:7 to 1:1), and thus 1.95 g (yield: 92%) of the title compound was obtained as colorless crystals.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=3:7 to 1:1)

Sources & evidence

ORD record
ord-c1c00d676b7245dfbbe02fd4f9c10d23
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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