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Hexane → tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamate

HRID 843259
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 843259
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31].CCCCCC>ClCCl>[N+:30]([C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:20]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:28][CH:27]=[CH:26][CH:25]=2)([O-:32])=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 112758084-Chloro-3-nitroquinoline

Produkt 1

HCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamateAusbeute 92.088,602 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

Triethylamine (66.8 g, 0.66 mmol) was added to a solution of tert-butyl (N-2-aminoethyl)carbamate (55.0 g, 0.34 mmol) in anhydrous dichloromethane (500 mL). 4-Chloro-3-nitroquinoline (68.2 g, 0.33 mmol) was slowly added. The reaction mixture exothermed. The reaction mixture was allowed to stir overnight. The resulting precipitate was isolated by filtration and rinsed with water to provide a yellow solid. The filtrate was washed with water, dried over magnesium sulfate and then concentrated to provide a yellow solid. The two batches of solid were combined, slurried with hexane, filtered and then dried to provide 101 g of 1,1-dimethylethyl N-{2-[(3-nitroquinolin-4-yl)amino]ethyl}carbamate as a yellow solid.

Aufarbeitung

  1. customThe resulting precipitate was isolated by filtration
  2. washrinsed with water
  3. customto provide a yellow solid
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto provide a yellow solid
  8. filtrationfiltered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-78495cd1f05645938669ccf585ac77d4
Quelldatensatz
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06376669B1

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