O-ethylhydroxylamine hydrochloride → 2-methyl-1-[(2-nitrobenzyl)oxy]-1H-imidazo[4,5-c]quinoline

HRID 2105495Notes

Reaction equation

HRID 2105495 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)[CH3:14].ClC1C2C(=CC=CC=2)N=CC=1NC=O.Cl.[N+:31]([C:34]1[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=1[CH2:36][O:37][NH2:38])([O-:33])=[O:32].Cl.C(ON)C>C(O)(C)C>[CH3:14][C:13]1[N:38]([O:37][CH2:36][C:35]2[CH:39]=[CH:40][CH:41]=[CH:42][C:34]=2[N+:31]([O-:33])=[O:32])[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]=1

Participants

6

Reactant 4

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 22255723O-(2-nitrobenzyl)hydroxylamine hydrochlorideHCID 67506066HCID 67506066, compoundHCID 86227468N-(4-chloroquinolin-3-yl)formamide

Product 1

HCID 675063822-methyl-1-[(2-nitrobenzyl)oxy]-1H-imidazo[4,5-c]quinolineYield 47.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The method of Part B of Example 20 was followed using N-(4-chloroquinolin-3-yl)acetamide (10.6 g, 48.0 mmol) in lieu of 4-chloroquinolin-3-ylformamide and O-(2-nitrobenzyl)hydroxylamine hydrochloride (10.8 g, 52.8 mmol) in lieu of O-ethylhydroxylamine hydrochloride in isopropanol (120 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 7.6 g of 2-methyl-1-[(2-nitrobenzyl)oxy]-1H-imidazo[4,5-c]quinoline.

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-2aeaf7cc9a124d3da43437566e588b78
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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