Benzyloxyamine hydrochloride → HCID 57429983, 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.[CH2:20]([O:27][NH2:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(O)C>[CH2:20]([O:27][N:28]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][O:15][CH2:16][CH3:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of N-(4-chloroquinolin-3-yl)-2-ethoxyacetamide (4.5 g, 18 mmol) and O-benzylhydroxylamine hydrochloride (4.3 g, 27 mmol) in propan-2-ol (100 mL) was heated at 60° C. for 2 days. The mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (150 mL) and saturated aqueous sodium bicarbonate (35 mL). The organic layer was dried over potassium carbonate, filtered, and evaporated to yield 5.7 g of crude 1-(benzyloxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline that was used directly in Part B.