8-Hydroxyquinoline → HCID 10181600, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([CH:20]=1)[CH:18]=O.[C:25](#[N:29])[CH2:26][C:27]#[N:28].C1N2CCN(CC2)C1>C(O)C.O>[NH2:29][C:25]1[O:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][N:10]=3)[CH:5]=[CH:4][C:3]=2[CH:18]([C:17]2[CH:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[C:13]([Br:12])[CH:20]=2)[C:26]=1[C:27]#[N:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
8-Hydroxychinoline (14.5 g, 100 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (20.4 g, 83.33 mmol) and malononitrile (5.5 g, 83.33 mmol) were taken in 250 ml ethanol at room temperature, charged with DABCO (917 μl, 8.33 mmol) and then stirred at 80° C. under LC-MS control for 18 days. The reaction mixture was cooled down to room temperature, diluted with water to about 500 ml and extracted with ethyl acetate (2×100 ml). The ethyl acetate solution was washed with 5% sodium bicarbonate solution (2×100 ml), dried over magnesium sulfate, solvent was then evaporated under vacuum at 40° C. and the solids were dried under high vacuum to yield 22.5 g (61.6%) of the title compound.
Workup
- temperatureThe reaction mixture was cooled down to room temperature
- extractionextracted with ethyl acetate (2×100 ml)
- washThe ethyl acetate solution was washed with 5% sodium bicarbonate solution (2×100 ml)
- dry with materialdried over magnesium sulfate, solvent
- customwas then evaporated under vacuum at 40° C.
- customthe solids were dried under high vacuum
Sources & evidence
- ORD record
- ord-b06e5547b15c49b3aff373d568ae139f
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371333B2
Reaction notes
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