O-ethylhydroxylamine hydrochloride → 1-phenoxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105498Notes

Reaction equation

HRID 2105498 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH3:16].ClC1C2C(=CC=CC=2)N=CC=1NC=O.Cl.[C:33]1([O:39][NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.C(ON)C>C(O)(C)C>[O:39]([N:40]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 6365179O-Phenylhydroxylamine hydrochlorideHCID 57447109HCID 57447109, compoundHCID 86227468N-(4-chloroquinolin-3-yl)formamide

Product 1

HCID 675061661-phenoxy-2-propyl-1H-imidazo[4,5-c]quinolineYield 37.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The method of Part B of Example 20 was followed using N-(4-chloroquinolin-3-yl)butyramide (3.5 g, 14 mmol) in lieu of 4-chloroquinolin-3-ylformamide and O-phenylhydroxylamine hydrochloride (2.3 g, 16 mmol) in lieu of O-ethylhydroxylamine hydrochloride in isopropanol (100 mL). Chromatographic purification was carried out eluting with 5% methanol in dichloromethane containing 2 mL of aqueous ammonium hydroxide per liter of eluent to provide 1.58 g of 1-phenoxy-2-propyl-1H-imidazo[4,5-c]quinoline as a brown, foamy solid.

Workup

  1. customChromatographic purification
  2. washwas carried out eluting with 5% methanol in dichloromethane containing 2 mL of aqueous ammonium hydroxide per liter of eluent

Sources & evidence

ORD record
ord-7ba2a300b49247cf9d903e123119f7aa
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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