Diethyl Malonate → HCID 67010948, compound

HRID 2194532Notes

Reaction equation

HRID 2194532 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]=O)[CH:3]=1.[C:16](OCC)(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].N1CCCCC1>C(O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([N:7]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][N:13]=3)[CH:14]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]2=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 87235637HCID 87235637, compound

Product 1

HCID 67010948HCID 67010948, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

3.3 g (16 mmol) of (2-(5-methyl-3-isoxazolyl)amino)nicotinaldehyde was dissolved in ethanol (60 mL), and 3.9 g (24 mmol) of diethyl malonate and 0.56 g (6.5 mmol) of piperidine were added thereto. The resulting mixture was stirred overnight at 90° C. The reaction mixture was cooled, and then the solvent was distilled off. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 7:3), and thus 2.7 g of the title compound was obtained as pale yellow crystals (yield: 55%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationthe solvent was distilled off
  3. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 7:3)

Sources & evidence

ORD record
ord-197eb23dc7cb458f80380d741a620b34
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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