Org Prep Daily

September 20, 2006

3-Amino-2,4,6-collidine

Filed under: procedures — milkshake @ 9:48 pm

aminocollidine1.gif

2,4,6-collidine 15.0g (0.1238 mol) was added dropwise into 20% oleum 70mL in a 0.5L flask on ambient oil bath. (Quite exothermic). The mixture was brought up to 100 C and powdered potassium nitrate 30g was slowly added in small portions over 15 minutes (nitrous gas evolution). The mixture was stirred under a reflux condenser at 100 C for 5 hous, then cooled and poured on ice (400g). The mixture was made alkaline by adding concentrated aq. ammonia (300mL), cooled and extracted with dichloromethane (3x100mL). The combined extracts were dried (MgSO4) and evaporated. The residue (18g) was re-crystallized from pentane (60mL) at -20C (freezer 14 hours) to obtain 15.75g of pure nitrocollidine. A second crop (1.40g) was obtained by concentrating and cooling the supernatants. Y=17.15g (83.5%) of the nitrocollidine as a light-yellow crystalline solid.

 

The nitrocollidine 8.00g was hydrogenated in anhydrous ethanol 120mL over 10% Pd-C (3.6g) at 50psi in a Parr shaker for one day. (The hydrogen consumption ceased within 1 hour). The mixture was filtered through a pad of celite, filtrates evaporated and dried on highvac. The solid residue was dissolved in refluxing hexane, filtered while hot, diluted with additional hexane (50mL) and the allowed to crystallize in freezer at -20C overnight (16h). The supernatants were decanted off and the obtained pure aminocollidine was dried on highvac. Y=6.029g (92%) of a white shiny hygroscopic crystalline solid. 1H-NMR(CD3CN, 400MHz): 6.715(s,1H), 3.784(br s, 2H), 3.377(s, 3H), 2.265(s, 3H), 2.081(s, 3H)

 

4 Comments »

  1. Whoa, this is totally awesome. Is this the same milkshake from the Scripps in Jupiter? You’ve earned yourself a spot on my blogroll, buddy. You should seriously consider, however, looking up Chemaxon to create and store a web accessible database of all this awesome shittery you’re posting. If you would like to collaborate, I’d be more than happy to help.

    Comment by Kyle Finchsigmate — September 21, 2006 @ 1:31 am

  2. Hi Kyle – it is me. Searching: I would wait a month or two, to see if I won’t get tired of it (like Dylan). And if I don’t, I could put up chemical categories (i.e. reagents, reduction, Suzuki coupling, chiral building blocks, amines), and tag them to each procedure.

    I don’t know about running a searchable database myself. I am computer-illiterate (flunked the COMP-101 class as undergrad) and it is hardly going to be a large procedure collection from my posting – that is unless some other people join in. (But if they do, we could have a nice private version of OrgSyn here🙂

    If you have a good preparative procedure (that is easy to do, reliable, scales up well, uses easy-to-get starting material etc.) I would very much encourage you to put it up here, if you want. My institute e-mail is tomasv@ …. edu

    Comment by milkshake — September 21, 2006 @ 2:17 am

  3. Hey I wouldnt mind to contribute as far you dont have me on your black list (like ACS with La…)🙂

    My only trouble is that posting some of that procedures, I would revealed my identity (even when I probably somebody could figured it out).Specially when soon I will have to write…

    Comment by HOMO-LUMO — September 21, 2006 @ 3:22 am

  4. H-L: Send me what you have – The procedures do not need to be original. The requirement is that the procedures are easy to do, reliable (you tried it couple times and it always worked), scalable, interesting and useful. Purification details, NMR spectra should be included. (Like a write-up to a contract lab: you would not want anybody to get stuck making the stuff for you.) OrgSyn is a good example.

    If you are working on a total synthesis project, the most suitable procedures would probably entail the reagents, the building blocks and the initial 2-3 steps that are necessarily run in multigram quantities, to push the material through. You should not publish anything that would put you and your project in jeopardy. Academic groups and companies alike are furious when scooped by competition (because details of work in progress were leaked). Use common sense.

    Comment by milkshake — September 21, 2006 @ 4:12 am


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