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Dimethylformamide → Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887721
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887721
Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=[C:9]([Br:13])[CH:10]=2)[NH:5][C:4]1=[O:17].CN(C=O)C.C(N(CC)CC)C.[C:30](=O)([O:36]C(C)(C)C)[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>O>[Br:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1)[NH:5][C:4](=[O:17])[CH:3]([NH:2][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:12]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 684113113-amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride

Produkt 1

HCID 59620339Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamateAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Versuchsvorschrift

3-Amino-6-bromo-8-nitro-3,4-dihydroquinolin-2(1H)-one hydrochloride (610 g) was added to N,N-dimethylformaldehyde (3 L), and triethylamine (554 mL) was added dropwise to the mixture under cooling on ice. Subsequently, di-tert-butyl carbonate (454 g) was added thereto, and the resultant mixture was stirred at room temperature for 30 minutes. Water (3 L) was added to the reaction mixture, and stirring was performed for 30 minutes under cooling on ice. The precipitates were recovered through filtration and washed sequentially with water and diisopropyl ether. The thus-obtained solid was dried, whereby the title compound (674 g) was yielded as a powdery compound.

Aufarbeitung

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling on ice
  3. temperatureunder cooling on ice
  4. filtrationThe precipitates were recovered through filtration
  5. washwashed sequentially with water and diisopropyl ether
  6. customThe thus-obtained solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-99bf8dcfcd0e4d79aaef1e41629e7c40
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501772B2

Notizen zur Reaktion

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