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Reaction id: 0801011014_09, verified by Personal Chemistry ©
4-Hydroxybenzald...
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3-(Cyanoacetyl)i...
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Ammonium ac...
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Ethylene glycol
Acetic acid
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9
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Yield: 83% Time: 720s Temperature: 140 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 123-08-0 |
122.123 |
1.000 |
1.000 |
122.123 mg |
| 20356-45-0 |
184.198 |
1.000 |
2.000 |
368.396 mg |
| Ammonium acetate |
77.083 |
1.000 |
5.000 |
385.415 mg |
| Acetic acid |
60.052 |
1.050 |
8.742 |
500.000 µl |
| Ethylene glycol |
62.068 |
1.113 |
17.932 |
1000.000 µl |
| Product 1 |
451.489 |
1.000 |
0.000 |
0.000 mg |
Keywords
Condensation, Cyclisation, Heterocyclic, Heterocyclisation, Multicomponent, Ring closure, Ring formation
Comments
Synthesis: This method was found to be very general for a number of aromatic and heteroaromatic aldehydes, with different types of substituents, and also for the substituted 3-(cyanoacetyl)indoles tested. It did not work with aliphatic aldehydes as starting materials. When attempted using conventional heating, the example reaction was refluxed for 12 h and gave 47% yield, to compare with 80% using microwave heating.
The maximum power was set to 250 W for this reaction.
Work-up and purification: After the reaction, the mixture was poured into 100 ml cold water. The product was filtered off and washed with ethanol, and then purified by recrystallisation from ethanol-DMF (1/1).
Characterisation: By mp, IR, 1H and 13C NMR and HRMS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Zhu, S.-L.; Ji, S.-J.; Su, X.-M.; Sun, C.; Liu, Y. Tet. Lett. 2008, 49, 1777-1781
Analysis
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