Bicyclo(2.2.1)heptan-2-one → HCID 21960027, compound

HRID 2253625Notes

Reaction equation

HRID 2253625 reaction equation
C(#N)C1[C:3](=[CH:5]C=[CH:7][CH:8]=1)[NH2:4].[CH2:10]1C2[CH2:15][C:16](=[O:17])C(C2)[CH2:11]1.[OH-:18].[Na+]>[Cl-].[Cl-].[Zn+2].ClCCCl>[NH:4]([CH2:3][CH3:5])[CH2:10][CH3:11].[CH3:15][CH2:16][O:17][C:7]([CH3:8])=[O:18]

Participants

6

Reactant 3

HCID 10345Bicyclo(2.2.1)heptan-2-oneHCID 14798Sodium HydroxideHCID 729132-Aminobenzonitrile

Product 1

HCID 21960027HCID 21960027, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

Anthranilonitrile (2.40 g) was mixed together with norcamphor (4.40 g) and then 4.0 g of freshly fused ZnCl2 was added and the reaction mixture was heated at 120° C. After 1.5 hours it became so thick that it could not be stirred, so 10 ml of 1,2-dichloroethane was added and the reaction mixture was refluxed for 1 hour. At the end of this time, 40 ml of 10% NaOH was added and the mixture was stirred overnight. It was then extracted several times with 2-butanone which gave a crude product that was purified by flash chromatography (EtOAc, then 5% Et2NH/EtOAc) to give 3.04 g of foam. Recrystallization from CH2Cl2 /pentane gave 2.30 g of analytically pure product, m.p. 186°-188°.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was refluxed for 1 hour
  3. extractionIt was then extracted several times with 2-butanone which
  4. customgave a crude product that
  5. customwas purified by flash chromatography (EtOAc

Sources & evidence

ORD record
ord-eac473f4b9b34d3b981c56f3ba44bc1b
Source dataset
uspto-grants-1993_08
Patent number
US05232927

Reaction notes

Loading…