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

HRID 1846412Notes

Reaction equation

HRID 1846412 reaction equation
[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]

Participants

7

Reactant 4

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

Product 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 oximeYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c4297c434f0d4a90932e3619d5a37a16
Source dataset
uspto-grants-2015_02
Patent number
US08952033B2

Reaction notes

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