So, at first it was thought that it would bee best to run a full series of rxns with different catalysts, but then she thought that, really, Pd/C is much cheaper and more common than Rh/Barium or Pt/C for the average chemist so that really isn't the way to go unless Pd/C simply can't do the job excellently, which I don't believe is the case. Raney nickel was also an option but the experimentor was not familiar with the neccessary catalyst loading or safety issues and also she got the impression that it was inferior anywayz. Maybe somebody might convince her that Ni would bee worth trying. Those arguements are welcome...
So, 1st trial:
39 g or .219 moles 'tone
2 equivalents of MeNH4Cl
2 equivalents of triethylamine
4+ equivalents of formic
2 equivalents of NaOH
10 g 10% Pd/C
100 mL MeOH
250 mL IPA
40 mL H2O
She added the 'tone last after the temp had cooled down and let stir. Then she left to get a drink with some friends and then thought "oh no! Might the 'tone bee reduced to an alcohol b4 it gets a chance to form the imine?" But a friend said (in a simplified sense) that Pd would much rather reduce an imine than a 'tone and so she needn't worry. When she returned an hour or two later, she put the rxn flask and a beaker w/ 300 mL water in a regular microwave, set it on medium, and proceeded to microwave for 1 minute increments ten times. She did this all because of her excitement after reading that microwave paper mentioned by I-forget-who. Well, the microwave was definitely not beneficial. Another ~36 hours until there was no more noticable bubbles (even very small ones) and after work-up, the product oil was a bit on the dark side. Sunlight was absolutely right, heat is not good for this rxn, and microwaves are not a shorter route to product in this rxn. Yield 55%. Oh, and another thing realized is that triethylamine is a bitch to get rid of. It was used instead of K+ ion because she felt it would help drive imine formation and thus require less methylamine. Not worth it IMO.
2nd trial:
39 g 'tone
3.4 equivalents of MeNH2 (aq)
1.86 equivalents of MeNH3Cl
5 equivalents of KOH
formic acid until pH=6
325 mL MeOH
160 mL IPA
90 mL water (including aq. MeNH2)
10 g 10% Pd/C (used in the previous rxn, stored wet with water)
Notice both my higher ratio of water to solvent and the use of less overall solvent than Sunlight. I believe the latter is crucial to using less catalyst. This time the 'tone was added second, after the aq. MeNH2. This will not bee done again because she felt it is prolly rough on the 'tone with all the base and acid adding and resultant heat. The solution was cooled in a bath to a bit below r.t. and then the Pd/C was added and added slowly because the resultant release of CO2 was intense. The rxn ran for the first 12 hours in a mostly closed hood about 8-10 inches from another reaction that was refluxing in a 150 °C oil bath- dummy. The flask wasn't all that warm upon checking, but still, it is obvious that heat is not desirable. Results will bee in soon.
Improvements: She thinks a more intelligent way would bee adding everything but 'tone and Pd/C, while cooling to 0 °C in an ice bath, adding the 'tone, stir for an hour (paranoia), add Pd/C (still in ice bath) and let warm to r.t. over rxn period of ~36-48 hours, basically until absolutely no teeny tiny bubbles are noted.
Is storing Pd/C wet with dH2O the best way???
I, of course, give mad props to Sunlight, for any possible improvement would bee based on his/her work....