Triethylamine → 1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanol

HRID 44706

Reaktionsgleichung

Reaktionsgleichung von HRID 44706
[NH2:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]>ClCCl>[N+:26]([C:17]1[CH:18]=[N:19][C:20]2[C:25]([C:16]=1[NH:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1)=[CH:24][CH:23]=[CH:22][CH:21]=2)([O-:28])=[O:27]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 112758084-Chloro-3-nitroquinolineHCID 282600091-(Aminomethyl)cyclobutan-1-ol

Produkt 1

HCID 574578111-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(aminomethyl)cyclobutanol (62.5 mmol) in dichloromethane (312 mL) was added triethylamine (8.71 mL, 62.5 mmol) and 4-chloro-3-nitroquinoline (13.04 g, 62.5 mmol). More triethylamine (3 mL) was added almost immediately. The reaction was stirred under N2 for 10 d at rt, then was diluted with dichloromethane and washed with 1 M aqueous NaOH. A solid formed and was isolated by filtration. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to a solid that was crystallized from isopropanol. The resulting crystals were combined with the solid that was isolated from the extraction and the mixture was triturated with hot isopropanol. The solid was isolated by filtration, washed with diethyl ether, and air dried to yield 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclobutanol as yellow crystals. (12.83 g, 75%).

Aufarbeitung

  1. washwashed with 1 M aqueous NaOH
  2. customA solid formed
  3. customwas isolated by filtration
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to a solid
  8. customthat was crystallized from isopropanol
  9. customthat was isolated from the extraction
  10. customthe mixture was triturated with hot isopropanol
  11. customThe solid was isolated by filtration
  12. washwashed with diethyl ether, and air
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-220d0047b7ff4594bc9afa7e60146efa
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541438B2

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