Reaktion #1519150

ord-baa79eb8954e4217a9cf27cd3e00b0b1

Reaktionsgleichung

[BH4-].[Na+]
sodium borohydride
c1ccc2ncccc2c1
quinoline
CC(=O)O
acetic acid
CC(=O)N1CC=Cc2ccccc21
expected product
CC(=O)N1CC=Cc2ccccc21
1-Acetyl-1,2-dihydroquinoline

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is then heated for 2 hours at 60° C.
  2. 2
    EinengenThe mixture is concentrated
  3. 3
    workup.ADDITIONdiluted with water
  4. 4
    Extraktionextracted with ether
  5. 5
    WaschenThe combined ethereal phases are washed with 1N hydrochloric acid

Vorschrift

23.43 g of sodium borohydride are introduced, in portions, into a solution of 20 g of quinoline in 200 ml of acetic acid and 77.5 ml of acetic anhydride, cooled to 0° C. The mixture is then heated for 2 hours at 60° C. and is stirred overnight at ambient temperature. The mixture is concentrated, diluted with water, adjusted to pH=10 with sodium hydroxide solution and extracted with ether. The combined ethereal phases are washed with 1N hydrochloric acid and then at neutral pH and after conventional treatment the expected product is isolated.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07612061B2uspto-grants-2009_11