Malononitrile → HCID 69093875, compound

HRID 2206280Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH: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:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[N:10]=3)[CH:5]=[CH:4][C:3]=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

8-Hydroxyquinaldine (382 mg, 2.4 mmol), 5-bromo-3,4-dimethoxybenzaldehyde (490 mg, 2 mmol) and malononitrile (132 mg, 2 mmol) were taken in 25 ml ethanol at room temperature, charged with DABCO (22 μl, 0.3 mmol) and then stirred at 80° C. under LC-MS control for 3 days. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and then extracted with ethyl acetate (2×50 ml). The organic solution was washed with 5% sodium bicarbonate solution (2×50 ml) and then dried over magnesium sulfate, solvent was evaporated under vacuum at 40° C. and the residue was dried under high vacuum giving 217 mg of the title compound (0.48 mmol, 20%).

Workup

temperatureThe reaction mixture was cooled down to room temperature
extractionextracted with ethyl acetate (2×50 ml)
washThe organic solution was washed with 5% sodium bicarbonate solution (2×50 ml)
dry with materialdried over magnesium sulfate, solvent
customwas evaporated under vacuum at 40° C.
customthe residue was dried under high vacuum

Sources & evidence

ORD record: ord-8c2f914612424a1eb1e2b06c551fa186
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371333B2

Reaction notes

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