Water → 3-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-ol

HRID 415479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415479
[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.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].O>CN(C=O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 27851382,4-Dichloro-3-nitroquinoline

Produkt 1

HCID 866337273-[(2-Chloro-3-nitroquinolin-4-yl)amino]propan-1-olAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2,4-dichloro-3-nitroquinoline (32 g, 130 mmol) in DMF (100 mL) was cooled to 0° C. Triethylamine (27.5 mL, 198 mmol) was added, and 3-amino-1-propanol (11.9 g, 158 mmol) was slowly added. The reaction was stirred for two hours at room temperature and cooled again to 0° C. Water (300 mL) was added, and the mixture was stirred for 30 minutes at 0° C. A solid was present and was isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 34.5 g of 3-[(2-chloro-3-nitroquinolin-4-yl)amino]propan-1-ol as a yellow and orange solid.

Aufarbeitung

  1. temperaturecooled again to 0° C
  2. stirringthe mixture was stirred for 30 minutes at 0° C
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried overnight in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-8446300024784402879d685d00a6e239
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088790B2

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