Malonic Acid → HCID 53401612, compound

HRID 2207901Notes

Reaction equation

HRID 2207901 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][N: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]=[C:6]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 27629912-Bromo-4-pyridinecarboxaldehyde

Product 1

HCID 53401612HCID 53401612, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-pyridin-4-carbaldehyde (20.0 g, 107.5 mmol), malonic acid (25.2 g, 241.9 mmol), and piperidine (8.8 mL, 89.2 mmol) were added to pyridine (65.2 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 dried under reduced pressure to give 18.2 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 dried under reduced pressure

Sources & evidence

ORD record
ord-30b3c9806cee410c831d6b4d2c327f51
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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