[nickpapa]

I am treating 5-chloro-1H-pyrrolo[2.3-b]pyridine-3-carbaldehyde with nitromethane and ammonium acetate, refluxing overnight. I concentrated the mixture, and when attempting to extract, the mixture just formed an emulsion and wouldn't dissolve in anything. I partitioned it in water and ethyl acetate, noting. I then tried DCM, diethyl ether, THF...and still nothing. Any suggestions? I am currently rotovapping off all the solvents and water to see if methanol has any solubility.

[kriggy]

From top of my head:
1) you can wait to see if the suspension goes away (might take a lot of time)
2) you can add NaCl into the aq. phase to improve the layer separation
3) you can use hairdryer to carefuly heat the separation funnel near the stopcock (takes some time to separate)
4) you can filter it through sintered glass
5) try to sonificate the mixture for a bit

What worked for me are 1/2/3 the others are that I heard of or worked for my friends.

[nickpapa]

@kriggy I let everything sit last night and nothing. I added NaCl to the aqueous layer and still nothing. I also stirred and heated to mixture and still nothing. I will try filtering off the solid and see what happens then.

[kriggy]

YOu can also evaporate the mixture to dryness and then add water + ethyl acetate or whatever you will be extracting with

[Enthalpy]

Centrifuge?

[eskil]

Did you follow a published procedure to make the nitrostyrene? In that case what's the ref? You can use methanol as solvent and alkylamine as a catalyst, see: J. Org. Chem. 18, 1-3 (1953)


Best,
eskil