Malonic Acid → 3-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazole

HRID 54542Notes

Reaction equation

HRID 54542 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH:14]=O)[N:10]=2)=[CH:5][CH:4]=1)#[N:2].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1>N1C=CC=CC=1>[C:18](/[CH:17]=[CH:14]/[C:11]1[N:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[O:13][N:12]=1)([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 199593005-(4-Cyanophenyl)-3-formyl-1,2,4-oxadiazole

Product 1

HCID 199592323-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazoleYield 49.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(4-cyanophenyl)-3-formyl-1,2,4-oxadiazole (2.0 g), malonic acid (4.18 g) and piperidine (0.50 ml) in pyridine (20 ml) was refluxed for 1 hour. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate, acidified to pH 2.0 with 4N hydrochloric acid washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from ethanol to give 3-{(E)-2-carboxyvinyl}-5-(4-cyanophenyl)-1,2,4-oxadiazole (1.2 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customthe mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-509f05d793794f72910ac3ffb024986c
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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