O-(propan-2-yl)hydroxylamine hydrochloride → HCID 67506144, compound
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][O:15][CH2:16][CH3:17].Cl.[CH:20]([O:23][NH2:24])([CH3:22])[CH3:21]>C(O)C>[CH2:16]([O:15][CH2:14][C:13]1[N:24]([O:23][CH:20]([CH3:22])[CH3:21])[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)[CH3:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-(4-chloroquinolin-3-yl)-2-ethoxyacetamide (7.3 g, 28 mmol) and O-isopropylhydroxylamine hydrochloride (3.3 g, 0.030 mol) in ethanol (150 mL) was heated at reflux for two hours, allowed to cool to room temperature, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 4% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent) to provide 2.15 g of 2-(ethoxymethyl)-1-isopropoxy-1H-imidazo[4,5-c]quinoline as a dark oil that crystallized upon standing.