[java]

I'm not sure if in the methylation of a primary aromatic amine  procedure using Paraformaldehyde and then catalytic Hydrogenation using Pd/C 10% in ethanol makes any difference, if the starting amine is a base or and HCl salt ....I would think it would't matter but not sure....any thoughts....java

[lavoisier]

I think you need at least some free amine to form the imine at a reasonable rate. Therefore I would first try with the HCl salt. If it doesn't work, I would add some base (TEA? Na2CO3? NaOAc?).

Classic reductive amination, as far as I can recall, can be done at pH 4-5 with NaBH(OAc)3, which means you still have some free amine at this relatively low pH. With an aromatic amine, it's even better, because it's a much weaker base than aliphatic amines.

If it really doesn't work with the amine.HCl (/+ base), just isolate the free base first.