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Ethanol → Tert-butyl 8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887722
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887722
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:5]2.C(O)C.C([O-])=O.[NH4+]>[Pd].O1CCCC1>[NH2:12][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:5]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 59620339Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Produkt 1

HCID 59620337Tert-butyl 8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamateAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

tert-Butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (628 g) was added to ethanol (3.1 L), and the mixture was heated at 65° C. To the mixture, 10% Pd—C (water content: 53%) (67.1 g) and ammonium formate (1.03 kg) were sequentially added, and the resultant mixture was stirred for 10 minutes under heating and reflux. Tetrahydrofuran (2.5 L) was added to the reaction mixture so as to dissolve the precipitates, and undissolved matter was removed through filtration with Celite. The filtrate was concentrated under reduced pressure, and water was added to the residue. The formed precipitates were recovered through filtration. The thus-obtained solid was dried, whereby the title compound (418 g) was yielded as a powdery compound.

Aufarbeitung

  1. temperatureunder heating
  2. temperaturereflux
  3. dissolutionto dissolve the precipitates, and undissolved matter
  4. customwas removed through filtration with Celite
  5. concentrationThe filtrate was concentrated under reduced pressure, and water
  6. additionwas added to the residue
  7. customThe formed precipitates
  8. filtrationwere recovered through filtration
  9. customThe thus-obtained solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-4fca78a441c04d61a50c9deeb4af89f3
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501772B2

Notizen zur Reaktion

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