Diethyl Malonate → Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

HRID 2194507Notes

Reaction equation

HRID 2194507 reaction equation
[CH:1]([C:3]1[C:4]([NH:9]C(=O)C(C)(C)C)=[N:5][CH:6]=[CH:7][CH:8]=1)=O.[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20]CC)=O.N1CCCC1>C(O)C>[O:20]=[C:18]1[C:17]([C:16]([O:24][CH2:25][CH3:26])=[O:23])=[CH:1][C:3]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:9]1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 31268PyrrolidineHCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

Product 1

HCID 11564777Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

6.57 g (32 mmol) of 3-formyl-2-(pivaloylamino)pyridine was dissolved in ethanol (50 mL), and 10.2 g (64 mmol) of diethyl malonate and 1.6 mL (16 mmol) of pyrrolidine were added to the above solution. The resulting mixture was stirred overnight at 100° C. The reaction mixture was cooled to room temperature, and a solid precipitated therefrom was washed with ethanol. Thus, 2.2 g (yield: 32%) of the title compound was obtained as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customa solid precipitated
  3. washtherefrom was washed with ethanol

Sources & evidence

ORD record
ord-0f4c1c8bc6d0478c8793c7cf282689b5
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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