Diethyl Malonate → HCID 66737111, compound

HRID 2096121Notes

Reaction equation

HRID 2096121 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([F:10])=[CH:4][N:3]=1.[C:11](OCC)(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].N1CCCCC1>C(O)C>[F:10][C:5]1[CH:6]=[C:7]2[C:2](=[N:3][CH:4]=1)[NH:1][C:11](=[O:18])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8]2

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 497615922-Amino-5-fluoro-pyridine-3-carbaldehyde

Product 1

HCID 66737111HCID 66737111, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-fluoropyridine-3-carboxaldehyde (2.80 g), diethyl malonate (6.40 g) and piperidine (0.85 g) in ethanol (50 ml) were heated to reflux with stirring for 18 hours, allowed to cool to ambient temperature then evaporated under reduced pressure. The residual solid obtained was washed with diethyl ether then filtered from solution, and sucked to dryness to give the required product as a pale brown solid, 3.97 g. 1H NMR (CDCl3) δ: ca 11.0 (1H, bs), 9.33 (1H, m), 8.66 (1H, d), 8.42 (1H, s), 7.74 (1H, m), 4.45 (2H, q), 1.44 (3H, t).

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. customthen evaporated under reduced pressure
  4. customThe residual solid obtained
  5. washwas washed with diethyl ether
  6. filtrationthen filtered from solution

Sources & evidence

ORD record
ord-50c3a139f6374b10bab4b5b884e6da04
Source dataset
uspto-grants-2013_05
Patent number
US08450243B2

Reaction notes

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