Hydrochloric Acid → 1-(4-(Furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-2-aminoethyl oxime

HRID 1846412

Reaktionsgleichung

Reaktionsgleichung von HRID 1846412
[O:1]1[C:5]2=[N:6][C:7]3[C:12]([C:13]([NH:14][C:15]4[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=4)=[C:4]2[CH:3]=[CH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[NH2:24][CH2:25][CH2:26][O:27][NH2:28].Cl.C([O-])([O-])=O.[K+].[K+]>CCO>[O:1]1[C:5]2=[N:6][C:7]3[C:12]([C:13]([NH:14][C:15]4[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=4)=[C:4]2[CH:3]=[CH:2]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[NH2:24][CH2:25][CH2:26][O:27][N:28]=[C:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]3[O:1][CH:2]=[CH:3][C:4]=23)=[CH:16][CH:17]=1)[CH3:22]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4043531-(4-(Furo(2,3-b)quinolin-4-ylamino)phenyl)ethanoneHCID 4620742-(Aminooxy)ethanamine

Produkt 2

HCID 4043531-(4-(Furo(2,3-b)quinolin-4-ylamino)phenyl)ethanoneHCID 760235401-(4-(Furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone O-2-aminoethyl oximeAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-(4-(furo[2,3-b]quinolin-4-ylamino)phenyl)ethanone (compound 1) was prepared according to the method as described in Example 4 of U.S. Pat. No. 6,750,223 B2. The thus obtained compound 1 (0.30 g, 1 mmol), 2-aminoethoxyamine.HCl (0.28 g, 2.5 mmol), and K2CO3 (0.69 g, 5.0 mmol) were added into EtOH (10 mL). The resultant mixture was subjected to reflux for 4 hours (TLC monitoring), followed by evaporation under reduced pressure. The residue thus acquired was dissolved in CH2Cl2 (50 mL). The CH2Cl2 layer was washed sequentially with H2O and brine, was dried using Na2SO4, and was subjected to an evaporation treatment. The resultant residue was purified via flash column chromatography (MeOH/CH2Cl2=1/50), followed by recrystallization from EtOH. The title compound 13a as a light yellow solid (0.45 g, 96% yield) was obtained.

Aufarbeitung

  1. temperatureto reflux for 4 hours (TLC monitoring)
  2. customfollowed by evaporation under reduced pressure
  3. dissolutionThe residue thus acquired was dissolved in CH2Cl2 (50 mL)
  4. washThe CH2Cl2 layer was washed sequentially with H2O and brine
  5. customwas dried
  6. customThe resultant residue was purified via flash column chromatography (MeOH/CH2Cl2=1/50)
  7. customfollowed by recrystallization from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-c4297c434f0d4a90932e3619d5a37a16
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952033B2

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