Cyclohexylamine → 3-Quinolinecarboxamide, 1,2-dihydro-N-cyclohexyl-4-hydroxy-2-oxo-

HRID 346644

Reaktionsgleichung

Reaktionsgleichung von HRID 346644
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:24])[NH:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)C>C1(C)C=CC=CC=1.O>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:24])[NH:15][C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 7965CyclohexylamineHCID 54684458Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Produkt 1

HCID 546801053-Quinolinecarboxamide, 1,2-dihydro-N-cyclohexyl-4-hydroxy-2-oxo-Ausbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Cyclohexylamine (13.88 mL, 121.33 mmol) was added to a solution of Compound 112 (9.4 g, 40.44 mmol) in toluene (200 mL) and refluxed for 4 h. The solution was cooled and the solvent was evaporated under vacuum. The residue obtained was suspended in water, briefly sonicated, and filtered. The crude product was recrystallized by ether to yield 10.1 g (87%) of white solids. M.P. 223° C. 1H NMR (DMSO-d6): δ 1.3 (m, 4H), 1.6 (m, 2H), 1.7 (m, 2H), 1.9 (m, 2H), 3.8 (m, 1H), 7.25 (t, J=7.7 Hz, 1H), 7.35 (d, J=8.3 Hz, 1H), 7.65 (t, J=7.2 Hz, 1H), 7.95 (d, J=7.7 Hz, 1H), 10.44 (b, 1H); EIMS (neg. mode): 285 (M−H).

Aufarbeitung

  1. temperaturerefluxed for 4 h
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue obtained
  5. custombriefly sonicated
  6. filtrationfiltered
  7. customThe crude product was recrystallized by ether

Quellen und Nachweise

ORD-Eintrag
ord-67364dec13c94297b5be354191005dda
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173036B2

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