Carbon Dioxide → 3-(4-Pyridine)acrylic acid

HRID 1938786Notes

Reaction equation

HRID 1938786 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.C(=O)=O>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 8082PiperidineHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 7367823-(4-Pyridine)acrylic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-pyridine carboxaldehyde (36.7 mL, 0.384 mol) and malonic acid (40g, 0.384 mol) in 31 mL of pyridine was added piperdine (0.12 mL) and the mixture was warmed to 100° C. Caution: large volumes of CO2 evolved. After 0.5 h, the reaction was cooled to room temperature (RT) and the solution solidified. This was triturated with 240 mL of water and filtered, and washed with 2×50 mL portions of water. The solid was dried overnight at 42° C. under vacuum (10 mm Hg) to provide 37.1 g of a white solid; mp 295°-297° C.

Workup

  1. temperaturethe reaction was cooled to room temperature (RT)
  2. customThis was triturated with 240 mL of water
  3. filtrationfiltered
  4. washwashed with 2×50 mL portions of water
  5. customThe solid was dried overnight at 42° C. under vacuum (10 mm Hg)

Sources & evidence

ORD record
ord-0ba5cb14a04e4d1ca95cd0107302af62
Source dataset
uspto-grants-1997_12
Patent number
US05693803

Reaction notes

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