Diethyl Malonate → Ethyl 1,2-dihydro-2-oxo-1-phenyl-1,8-naphthyridine-3-carboxylate

HRID 2194527Notes

Reaction equation

HRID 2194527 reaction equation
[C:1]1([NH:7][C:8]2[N:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](OCC)(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].N1CCCCC1>C(O)C>[O:23]=[C:16]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:10][C:9]2[C:8](=[N:15][CH:14]=[CH:13][CH:12]=2)[N:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 13983610HCID 13983610, compound

Product 1

HCID 67010579Ethyl 1,2-dihydro-2-oxo-1-phenyl-1,8-naphthyridine-3-carboxylateYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

6.28 g (31.7 mmol) of 2-(phenylamino)nicotinaldehyde was dissolved in ethanol (150 mL), and 7.62 g (47.6 mmol) of diethyl malonate and 1.35 g (15.9 mmol) of piperidine were added thereto. The resulting mixture was stirred overnight at 100° C. The reaction mixture was cooled, and a solid precipitated thereby was separated by filtration. The solid was washed sequentially with ethanol and diisopropyl ether. Thus, 7.42 g of the title compound was obtained as a pale yellow solid (yield: 800).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customa solid precipitated
  3. customthereby was separated by filtration
  4. washThe solid was washed sequentially with ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-96944cf5db6744d3bc7dda3345aeedff
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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