Ammonia → 4'-Cyano-biphenyl-4-acetic acid

HRID 1004516

Reaktionsgleichung

Reaktionsgleichung von HRID 1004516
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N:18]1C=CC=C[CH:19]=1.N.O>CN(C=O)C>[C:19]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:18]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 962WaterHCID 1049PyridineHCID 13942454'-Bromo-4-carboxymethylbiphenyl

Produkt 1

HCID 230052184'-Cyano-biphenyl-4-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound (840 mg) obtained in the above (2) is dissolved in DMF (7 ml), and thereto are added pyridine (10 μl) and cuprous cyanide (I) (410 mg), and the mixture is refluxed with stirring for 8 hours. To the mixture is further added cuprous cyanide (I) (410 mg), and the mixture is refluxed with stirring for 7.5 hours. After cooling, to the mixture is added a mixture of conc. aqueous ammonia (5 ml) and water (60 ml), and the precipitates are removed by filtration. The filtrate is concentrated under reduced pressure, and the pH value of the residue is adjusted to pH 11 with 1N aqueous sodium hydroxide solution, and washed twice with ether. The pH value of the residue is adjusted to pH 1 with conc. hydrochloric acid, and extracted three times with ethyl acetate. The organic layer is washed with a saturated brine, and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure to give the title compound (654 mg).

Aufarbeitung

  1. temperaturethe mixture is refluxed
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for 7.5 hours
  4. temperatureAfter cooling, to the mixture
  5. additionis added
  6. customthe precipitates are removed by filtration
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. washwashed twice with ether
  9. extractionextracted three times with ethyl acetate
  10. washThe organic layer is washed with a saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe desiccant is removed by filtration
  13. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-96f30e826d7348f78db2b6fe69057bad
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048854

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