[Polly Murs]

I'm using a naphthylamine which I bought as HCl salt. I'm meant to dissolve this in toluene but it doesn't dissolve. is this why there's 4 times as much of this stuff compared with my other starting material? also it's relfuxed overnight.

the next day I filtered everything through celite and concentrated the filtrate = the NMR spectrum was exactly the same as that from my previous step, i.e. starting material didn't react with the amine at all

any ideas?

perhaps I should try deprotonating the salt?

[discodermolide]

I'm using a naphthylamine which I bought as HCl salt. I'm meant to dissolve this in toluene but it doesn't dissolve. is this why there's 4 times as much of this stuff compared with my other starting material? also it's relfuxed overnight.

the next day I filtered everything through celite and concentrated the filtrate = the NMR spectrum was exactly the same as that from my previous step, i.e. starting material didn't react with the amine at all

any ideas?

perhaps I should try deprotonating the salt?

That salt will not dissolve in toluene!
If you need the free amine then neutralize the salt, then the cod. will dissolve in toluene.

[Polly Murs]

hey
weak or strong base?

I'm an amateur so apologies for dumb questions

[Arkcon]

If you were expecting to perform an organic synthesis in toluene, you should have purchased the free amine.  Now you have a lot of work to do:  adding sufficient base to neutralize the acid (strong or weak depending on how strong or weak the acid salt of naphthylamine is -- probably should just use slight stochimetric excess of 1 N NaOH -- unless that decomposes naphthylamine, you have to look it up.)  Then you will have to perform a solvent extraction, just like the beginners organic chem experiment, where you separate an organic acid, an organic base, and a neutral organic by shaking in a separatory funnel (you are, in some ways, doing that experiment in reverse.)  Then you will have to evaporate the solvent off, because such manipulations will always result in some loss, and you will have to weigh it out again.  Maybe you should just store this reagent for some other use and save your time by purchasing the correct form.

[Polly Murs]

hi,

I've just done an extraction, but maybe best to just purchase the freebase

[OC pro]

What is the other starting material?

[Jasim]

Rule of thumb: Salts go in aqueous solvents (or polar), freebases go in non-aqueous/non-polar solvents.

[Honclbrif]

Pretty much every amine salt I've tried has dissolved in DCM or chloroform.

/ask me about my beautiful ¹H NMR of triethylammonium chloride in CDCl₃

[fledarmus]

Depending on what reaction you are trying to run, you might be able to get away with just adding a weak organic base to your reaction. Triethylamine and di-isopropylethylamine are commonly used for that purpose. They are strong enough to pull the HCl away from your naphthylamine, which should get it to dissolve. If you want, you can filter off the triethylamine-hydrochloride salt, but in many cases this isn't even necessary.

[Dan]

I agree with fledarmus, you should be able to generate the free base in situ without any problems. Can you tell us what the reaction is?

[opsomath]

I just want to add: be really damn careful! Naphthylamine is a truly dangerous carcinogen, used to induce tumors in lab animals.

[Polly Murs]

sorry fro delay

I'm synthesising a pyridylpyridone scaffold, it's a mimic for blocking estrogen receptor.

I'm going to use sodium methoxide and deprotonate in situ.
will let you know how it goes