Pyridine → HCID 19916998, compound

HRID 1464759Notes

Reaction equation

HRID 1464759 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=O)=[CH:2]1.[C:14]([CH2:16]C(O)=O)#[N:15].C([O-])(=O)C.[NH4+].N1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)/[CH:9]=[CH:16]/[C:14]#[N:15])=[CH:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9740Cyanoacetic acidHCID 517165Ammonium AcetateHCID 45475263-(Thiophen-3-yl)benzaldehyde

Product 1

HCID 19916998HCID 19916998, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1.0 g of 3-(3-thienyl)benzaldehyde, 0.5 g of cyanoacetic acid, 15 mg of ammonium acetate and 1 ml of pyridine were dissolved in 1.5 ml of xylene, and the mixture was refluxed for 5.5 hours. The solvent was evaporated, and the residue was dissolved in a mixture of ethyl ether and water, then the resulting solution was acidified with diluted hydrochloric acid. The organic layer separated was worked up in a customary manner, and the product purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=7/1→5/1] to give 0.4 g of (E)-3-(3-thienyl)cinnamonitrile as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 5.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in a mixture of ethyl ether and water
  4. customThe organic layer separated
  5. customthe product purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=7/1→5/1]

Sources & evidence

ORD record
ord-a432d9fad4f04c78abc5f0244e733737
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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