Water → 1,4-Methanonaphthalen-2(1H)-one, 3,4-dihydro-

HRID 1580315

Reaktionsgleichung

Reaktionsgleichung von HRID 1580315
[CH:1]12[CH2:9][CH:4]([CH2:5][C:6]1=NO)[C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][C:2]2=1.[Na].[OH2:15]>C(O)C.C(Cl)(Cl)Cl>[CH:1]12[CH2:9][CH:4]([CH2:5][C:6]1=[O:15])[C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][C:2]2=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 5360545SodiumHCID 71356783N-(3,4-Dihydro-1,4-methanonaphthalen-2(1H)-ylidene)hydroxylamine

Produkt 1

HCID 5757641,4-Methanonaphthalen-2(1H)-one, 3,4-dihydro-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of benzonorbornen-2-one oxime (2g.) in absolute ethanol (120ml.) was heated to reflux under nitrogen and sodium metal (12 g.) was added in small portions with continuous stirring. The reaction mixture was then refluxed for 30 minutes. This viscous suspension was then cooled to room temperature, 100 ml. of water added and the reaction mixture agitated until a clear solution was obtained. This was extracted with ether and the ether extract worked up to give an oil which was dissolved in chloroform and extracted with 10% HCl solution. Removal of water and excess HCl under vacuum from this extract gave a white solid (1g., 40%). The white solid was analyzed by infra-red, nuclear magnetic resonance and elemental analysis techniques and was determined to be the 1,2,3,4-tetrahydro-1,4-methanonaphthalen-endo-2-amine hydrochloride, C11H14NCl (m.p. 230°-231°C). Basification of a sample of this material with 10% NaOH gave, on ether extraction, the required amine as a pale yellow oil which was also analyzed by infra-red, and nuclear magnetic resonance techniques, and the empirical formula was determined to be C11H13N.

Aufarbeitung

  1. temperatureto reflux under nitrogen
  2. temperatureThe reaction mixture was then refluxed for 30 minutes
  3. customwas obtained
  4. extractionThis was extracted with ether
  5. extractionthe ether extract
  6. customto give an oil which
  7. extractionextracted with 10% HCl solution
  8. customRemoval of water and excess HCl under vacuum from this extract

Quellen und Nachweise

ORD-Eintrag
ord-d65f1e309a404ed7b1c0b904e0fa3bf3
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03932512

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