Malonic Acid → HCID 54545488, compound

HRID 2207897Notes

Reaction equation

HRID 2207897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=O)[CH:3]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 147614724-Bromopyridine-2-carbaldehyde

Product 1

HCID 54545488HCID 54545488, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-pyridin-2-carbaldehyde (10.0 g, 53.5 mmol), malonic acid (12.5 g, 120.5 mmol), and piperidine (4.4 mL, 44.4 mmol) were added to pyridine (32.5 mL). The reaction mixture was stirred at 100° C. for 1 hour, concentrated under reduced pressure, and then distilled water was added thereto. The mixture was filtered and then the resulting solid was dried under reduced pressure to give 6.3 g of the titled compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondistilled water was added
  3. filtrationThe mixture was filtered
  4. customthe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-091fc3bf3e084bee88f4371705bbfb63
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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