Diethyl Malonate → HCID 53396436, compound

HRID 2097054Notes

Reaction equation

HRID 2097054 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[C:11](OCC)(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].N1CCCCC1>CCO>[CH2:16]([O:15][C:13]([C:12]1[C:11](=[O:18])[NH:1][C:2]2[C:7]([CH:8]=1)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=2)=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehyde

Product 1

HCID 53396436HCID 53396436, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-bromo-pyridine-3-carbaldehyde (4.00 g, 14.2 mmol), diethyl malonate (21.6 mL, 142 mmol) and piperidine (7.00 mL, 71.0 mmol) in EtOH (70 mL) was heated to reflux overnight. The mixture was cooled to room temperature and the solid was collected by filtration to give the title compound (2.41 g, 57%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 12.65 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.56 (d, J=2.4 Hz, 1H), 8.45 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-ad9384e23fc5401bbe64bbcfd60d6920
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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