Triethylamine → 1-{[(3-Nitroquinolin-4-yl)amino]methyl}cyclobutanol
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[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]1([OH:28])[CH2:27][CH2:26][CH2:25]1>ClCCl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][CH2:23][C:24]1([OH:28])[CH2:27][CH2:26][CH2:25]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]Participants
Procedure
A solution of 4-chloro-3-nitroquinoline (30.0 g, 144 mmol) in dichloromethane (350 mL) was cooled to 0° C. under a nitrogen atmosphere, and triethylamine (22.1 mL, 158 mmol) was added. A solution of 1-(aminomethyl)cyclobutanol (16.0 g, 158 mmol) in dichloromethane (130 mL) was then added over a period of one hour, followed by a rinse of dichloromethane (100 mL). The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was triturated in water (500 mL) and saturated aqueous sodium bicarbonate (200 mL) for two hours. A solid was present and was isolated by filtration, washed with a large amount of water, and dried in a vacuum oven at 55° C. to provide 38.7 g of 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclobutanol as a yellow solid.
Workup
- washa rinse of dichloromethane (100 mL)
- customThe solvent was removed under reduced pressure
- customthe residue was triturated in water (500 mL)
- waitsaturated aqueous sodium bicarbonate (200 mL) for two hours
- customwas isolated by filtration
- washwashed with a large amount of water
- customdried in a vacuum oven at 55° C.
Sources & evidence
- ORD record
- ord-b47c1df018134899bbd8f44a760744ac
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541438B2
Reaction notes
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