Hello,
I am having some trouble trying to reduce a benzene ring with a H3C-C=N-NH2 substituent, to a cyclohexane with the same substituent. The ring is attached to the carbon that is double bonded with the nitrogen. Apparently the hydrogenation, H2/1000psi with ru/rh at 100C, would affect the nitrogen-carbon double bond. Anyone have any ideas how to reduce without affecting the substituent? Thanks so much
To reduce a benzene ring with a H3C-C=N-NH2 substituent to a cyclohexane with the same substituent without affecting the substituent, you can try a method called catalytic transfer hydrogenation. Here's how you can carry out this reaction:
1. Start with your benzene ring compound with the H3C-C=N-NH2 substituent.
2. Choose a suitable solvent for the reaction. In this case, a polar solvent such as ethanol or methanol can be used.
3. Add your benzene ring compound to the solvent.
4. Prepare a mixture of a suitable hydrogen donor and a catalyst. The hydrogen donor can be a simple alcohol like isopropanol or ethanol.
5. Add the mixture of hydrogen donor and catalyst to the reaction flask containing the benzene ring compound.
6. Stir the reaction mixture vigorously to ensure proper mixing.
7. Heat the reaction mixture to a suitable temperature, typically around 80-100°C.
8. Monitor the progress of the reaction by taking small samples at regular intervals and analyzing them using techniques such as thin-layer chromatography or spectroscopy.
9. Once the desired reduction is achieved, stop the reaction by cooling the mixture and removing the catalyst. This can be done by simple filtration or extraction methods.
10. Purify the product by appropriate methods such as distillation or chromatography.
Catalytic transfer hydrogenation is a useful method for selectively reducing benzene rings while leaving other functional groups intact. By using a suitable hydrogen donor and catalyst, you can control the reduction without affecting the H3C-C=N-NH2 substituent. Remember to use proper laboratory techniques and safety precautions while performing the reaction.