Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | HCID 66637270 | HCID 66637270 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 57458161 | HCID 57458161 | 91.1% |
Reaction Steps
A mixture of 6-tert-butylquinoline 1-oxide (310 mg, 1.54 mmol), trimethylsilylcyanide (458 mg, 4.62 mmol), trimethylamine (312 mg, 3.08 mmol) in acetonitrile (3 ml) was stirred for 15 minutes at 120° C. under microwave irradiation. The mixture was applied to a silica gel column chromatography and eluted with hexane/EtOAc (20:1) to furnish the title compound (295 mg, 91% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.44 (9H, s), 7.68 (1H, d, J=8.8 Hz), 7.79 (1H, d, J=2.2 Hz), 7.94 (1H, d, J=2.2, 8.8 Hz), 8.11 (1H, d, J=8.8 Hz), 8.26 (1H, d, J=8.8 Hz) MS (ESI): m/z 211 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08134004B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-d5c30e034ba64844947094d9721484a6 |
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| Source note | uspto-grants-2012_03 |
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