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Results of the nitration of bis quinoline 14. All yields reported are for chromatographically pure material.
| entry | conditions | 16 (%) | 17a (%) | 17b (%) |
|---|---|---|---|---|
| 1 | HNO3, H2SO4, 0 °C | 10 | 31 | 9 |
| 2 | KNO3, H2SO4, 0 °C | 8 | 14 | 5 |
| 3 | Bu4NNO3, (F3CCO)2O, 0 °C → rt | 71 | -- | -- |
| 4 | NO2BF4, sulfolane, rt | -- | -- | -- |
| 5 | fuming HNO3, CH3SO3H, rt | -- | 22 | 5 |
| 6 | fuming HNO3, 0 °C | 12 | 52 | -- |
