Ethylenediamine → 2-Cyano-5-(diphenylmethyl)-pyridine

HRID 1390326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1390326
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1.C(N)[CH2:22][NH2:23]>CN(C)P(N(C)C)(N(C)C)=O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1)#[N:23]

Komponenten

4

Edukt 2

HCID 3301EthylenediamineHCID 227487852-Chloro-5-(diphenylmethyl)-pyridine

Produkt 1

HCID 227487762-Cyano-5-(diphenylmethyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

Heat a mixture of 16.5 g. (0.059 mole) of 2-chloro-5-(diphenylmethyl)-pyridine and 10.6 g. (0.059 mole) of cuprous cyanide in 120 ml. of hexamethylphosphoramide with stirring at 210°-220° C. for 7 hours. Pour the cooled reaction mixture into a solution of 200 ml. of ethylenediamine in 500 ml. of water, and extract with benzene. Wash the benzene extracts with 10% aqueous sodium cyanide, then with water, dry, treat with activated charcoal, filter, and concentrate to obtain 2-cyano-5-(diphenylmethyl)-pyridine. This compound is converted directly to the title compound by heating at reflux with 13 g. of potassium hydroxide pellets in 100 ml. water and 200 ml. ethylene glycol for 15 hours. Remove the ethylene glycol and water under reduced pressure, dissolve the residue in water, acidify with concentrated hydrochloric acid, and extract with chloroform. Dry the chloroform extracts. Concentrate the dried extracts to a residue and triturate the residue with isopropyl ether. Filter the solids, dry and recrystallize from ethanol to obtain 5-(diphenylmethyl)picolinic acid, m.p. 189°-191° C.

Aufarbeitung

  1. temperatureHeat
  2. additiona mixture of 16.5 g
  3. additionPour
  4. customthe cooled reaction mixture into a solution of 200 ml
  5. extractionof water, and extract with benzene
  6. washWash the benzene
  7. dry with materialwith water, dry
  8. additiontreat with activated charcoal
  9. filtrationfilter
  10. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-3fd9735455b840f69d8ff7d6102c4f33
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04138488

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