Hydrochloric Acid → 3-Phenylindole-2-carbonitrile

HRID 263063

Reaktionsgleichung

Reaktionsgleichung von HRID 263063
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].C(OC(=O)[CH:17]([C:25]#[N:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.[OH-].[K+]>O.CCOCC.C(O)C>[C:19]1([C:18]2[C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:1][C:17]=2[C:25]#[N:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 14797Potassium HydroxideHCID 228103Ethyl 2-cyano-3-phenylpropanoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 124120803-Phenylindole-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel5×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4.08 g. (0.044 mol) of aniline in 18 ml. of concentrated hydrochloric acid and 50 ml. of water was maintained below 5° while a solution of 3.00 g. (0.043 mol) of sodium nitrite in 10 ml. of water was added. This solution was then added to a mixture of 8.30 g. (0.041 mol) of α-cyanobenzenepropanoic acid ethyl ester, 50 ml. of ethanol, 100 ml. of water, and 18 ml. of 50% potassium hydroxide solution maintained below 0°. After stirring for an additional 20 minutes the reaction was diluted with water and shaken with ether. Some insoluble solid was removed by filtration and the ether layer was concentrated. The residue was heated on the steam bath for 4 hours with 60 ml. of acetic acid and 60 ml. of concentrated hydrochloric acid. The cooled reaction was diluted with water and extracted with dichloromethane. The extracts were dried, filtered over some silica gel and concentrated. Recrystallization of the residue from dichloromethane-hexane gave 3-phenylindole-2-carbonitrile as tan crystals, m.p. 137°-142°.

Aufarbeitung

  1. additionThis solution was then added to a mixture of 8.30 g
  2. customSome insoluble solid was removed by filtration
  3. concentrationthe ether layer was concentrated
  4. temperatureThe residue was heated on the steam bath for 4 hours with 60 ml
  5. customThe cooled reaction
  6. extractionextracted with dichloromethane
  7. customThe extracts were dried
  8. filtrationfiltered over some silica gel
  9. concentrationconcentrated
  10. customRecrystallization of the residue from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-59cd4715d355409f9aa5e6d3b8845c03
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04156016

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