Malonic Acid → 3-(5-Bromopyridin-3-yl)prop-2-enoic acid

HRID 2207892Notes

Reaction equation

HRID 2207892 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 27847353-(5-Bromopyridin-3-yl)prop-2-enoic acidYield 154.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-pyridin-3-carbaldehyde (15.0 g, 80.6 mmol), malonic acid (18.9 g, 181.4 mmol), and piperidine (6.6 mL, 66.9 mmol) were added to pyridine (48.9 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 28.4 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-cef87d08cec1481d9c16f09a397af3e0
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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