Sn/HCl
Ph.NO2 + 6[h] -------------------? Ph.Nh2 + 2H2O
Into a 500ml RB flask equipped with a reflux condenser, place 25g (21ml, 0.25mol) of nitro benzene & 45g of granular tin. Measure out 100ml Conc.HCl. Pour about 15ml down the condenser and shake the flask steadily. The mixture becomes warm & before long the reaction should be quite vigorous. If it boils very vigorously, moderate the reaction by immersing the flask in cold water. When the initial reaction slackens, add further 15ml logs, following the above workup, until all the HCl has been added. Heat the mixture on a boiling water bath for 30-60 minutes. During this reduction, particularly during the cooling, aniline chlorostannate may separate as a white/yellow crystalline complex.
Cool the flask to RT & gradually add 75g NaOH in 125ml dH2O; If the mixture boils, cool again. The hydroxide of tin, which is first precipitated, should all dissolve & the solution should be strongly alkali.
Equip the flask for a steam distillation & pass steam into the warm mixture until, after the distillate has ceased to pass over as a turbid liquid, a further 120ml of clear liquid is collected. Since aniline is 3% water soluble, it must be salted out with NaCl (about 20g per 100ml liquid). Transfer the distillate, saturated with NaCL, into a sep. funnel and extract twice with 40ml portions of ether. Distill off ether & distill fraction 180-184C. Yield, 18g, 97%
Now in going for toluidine, it might separate into a separate liquid layer that can just be separated.
Thoughts?
I don't think there is any way to get rid of the smell of the nitrotoluene. This stuff smells up the entire neighborhood, but the smell can be reduced with a vacuum pump leading to the drain so it goes into the sewer.
By the way, to separate the isomers of nitrotoluene: put the stuff in a bottle and seal (to keep stink in) and place in the freezer until it all solidifies. Then take it out and let it come to room temperature. The o isomer will return to liquid and the others will tend to stay semi-solid. It can be vacuum filtered. Do this twice and you have close to pure o isomer. Amazing how much you lose, but it would have been lost anyway.
I'm still working on the anthranilic from phthalimide. I've gotten it to work, but the yield is around 20% and unreliable. Never did get Methacosmic's method to work, even after he contacted me by mail. Phthalimide is relatively cheap, US$25 per kg is a normal price.
What did you wind up paying for tin?
Do you know of a commercial source of tin (as opposed to a chemical supplier source)?