Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Malononitrile | HCID 8010 | — |
| Reactant | Dabco | HCID 9237 | — |
| Reactant | 2-Methyl-8-hydroxyquinoline | HCID 13224 | — |
| Reactant | 3-Bromo-4,5-dimethoxybenzaldehyde | HCID 81379 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 69093875 | HCID 69093875 | 24% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371333B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-8c2f914612424a1eb1e2b06c551fa186 |
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| Source note | uspto-grants-2016_06 |
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