Water → HCID 86633725, Verbindung

HRID 388606

Reaktionsgleichung

Reaktionsgleichung von HRID 388606
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:23]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[CH:34][CH:33]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].O>CN(C=O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:39][CH2:38][C:35]2[CH:36]=[CH:37][C:32]([CH2:31][NH:30][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:33][CH:34]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinolineHCID 3354775tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamate

Produkt 1

HCID 86633725HCID 86633725, VerbindungAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2,4-dichloro-3-nitroquinoline (11.4 g, 47.1 mmol) in DMF (200 mL) was cooled to 0° C. Triethylamine (19.6 mL, 0.141 mol) and 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene (13.3 g, 56.5 mmol) were sequentially added, and the reaction was stirred for one hour and cooled again to 0° C. Water (300 mL) was added, and the mixture was stirred for 30 minutes at 0° C. and then extracted with dichloromethane. The dichloromethane fraction was concentrated under reduced pressure to provide 20 g of tert-butyl 4-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}benzylcarbamate as a red oil.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes at 0° C.
  2. extractionextracted with dichloromethane
  3. concentrationThe dichloromethane fraction was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f25d4495112342dba36373896b68b5e2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377957B2

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