5-Chloro-8-hydroxyquinoline → HCID 69093713, compound

HRID 2206295Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Br:13][C:14]1[C:15]([O:24][CH3:25])=[C:16]([O:22][CH3:23])[CH:17]=[C:18]([CH:21]=1)[CH:19]=O.[C:26](#[N:30])[CH2:27][C:28]#[N:29].C1N2CCN(CC2)C1>C(O)C.O>[NH2:30][C:26]1[O:12][C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][N:7]=3)[C:2]([Cl:1])=[CH:11][C:10]=2[CH:19]([C:18]2[CH:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[C:14]([Br:13])[CH:21]=2)[C:27]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 80 °C

Procedure

5-Chloro-8-hydroxyquinoline (790.2 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol) and then stirred at 80° C. under LC-MS control for 18 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the solid were collected by filtration. It was washed with 50% aqueous ethanol. The solids were taken in 15 ml 2-propanol and stirred at 60° C. for 10 minutes, cooled down by dipping the flask in an ice bath, the solids were filtered and dried under vacuum to get the pure title compound (1.25 g, 2.64 mmol, 60%).

Workup

temperatureThe reaction mixture was cooled down to room temperature
filtrationthe solid were collected by filtration
washIt was washed with 50% aqueous ethanol
stirringstirred at 60° C. for 10 minutes
temperaturecooled down
filtrationthe solids were filtered
customdried under vacuum

Sources & evidence

ORD record: ord-c6965fb5f3a54b5d8873f5bafe987cb6
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371333B2

Reaction notes

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