I need to do a Schiff base reaction starting from a ketone and 1,10-phenanthroline-5-amino. I've seen that both of these starting materials are not very soluble in methanol and ethanol, which is what solvent I have seen most of these type of reactions done in. I just cannot get 100 mg of my starting material up in 300 mL of methanol, and I'm trying to use dry solvents, so I would prefer a solvent that I don't have to use a ton.
The starting material is very soluble in DCM, chloroform, toluene, DMF, THF, and other solvents such as that.
Peyton Anne Champion, you can use DMSO but a few of it, let the reaction for 24 hours, after the reaction is completed cool it then pure it into ice.
Hint: for 1ml DMSO use 50gm of ice
If your starting materials (a ketone and 1,10-phenanthroline-5-amino) are not very soluble in methanol or ethanol, you might consider using alternative solvents that are more effective in dissolving these compounds. Here are a few suggestions:
1. Dimethyl Sulfoxide (DMSO):
- DMSO is a highly polar aprotic solvent that can dissolve a wide range of organic compounds. It might improve the solubility of your starting materials.
2. Dimethylformamide (DMF):
- DMF is another polar aprotic solvent known for its ability to dissolve many organic substances, including those that are poorly soluble in methanol or ethanol.
3. Acetonitrile (MeCN):
- Acetonitrile is a polar aprotic solvent that is less polar than DMSO and DMF but can still dissolve many organic compounds.
4. Tetrahydrofuran (THF):
- THF is a moderately polar solvent that is often used in organic synthesis. It can sometimes dissolve compounds that are not soluble in alcohols.
5. Chloroform (CHCl₃) or Dichloromethane (DCM):
- These non-polar solvents might help if your compounds have significant non-polar character.