1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol → 1-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol

HRID 547327Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547327
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:19])[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]>[Pt].C(OCC)(=O)C.CO>[N+:1]([C:4]1[C:5]([NH:14][CH2:15][C:16]2([OH:19])[CH2:18][CH2:17]2)=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]1([OH:19])[CH2:18][CH2:17]1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

5

Edukt 1

HCID 574554091-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclopropanol

Produkt 1

HCID 672039411-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclopropanol (3.50 g, 13.5 mmol) and 5% platinum on carbon (350 mg) in ethyl acetate (70 mL) and methanol (7 mL) was hydrogenated under 35 psi (2.4×105 Pa) on a Parr apparatus for 3 hours. The mixture was filtered through CELITE filter agent, which was rinsed with ethyl acetate. The filtrate was concentrated under reduced pressure to yield 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopropanol 1-{[(3-nitroquinolin-yl)amino]methyl}cyclopropanol an orange oil that was used immediately in the next step.

Aufarbeitung

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas rinsed with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5a01477051704c2e8c0bc83926f814e1
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939526B2

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