mordacious - 22-11-2004 at 19:52
hi 
i'm new here, looks like a great place 
i'm looking for any aromatic diazotination procedure that uses an aromatic amine. google came up with nothing (except for this lovely site) and i
will need it for my advanced synthesis lab. if time allows (5 hours) i will do the procedure, if not, i won't but will still need a procedure
anyways.
any help is appreciated!
- ashley
BromicAcid - 22-11-2004 at 21:06
Polverone has at least one book on his website, Vogel's practical organic chemistry or something to that extent that has a whole section on
diazotization reactions however his site is giving an error right now.
Of course the basic procedure involves reacting the amine with an acidified solution of sodium nitrite below 5 C to work. Is there any specific
compound you are shooting for? Maybe you didn't get any good hits on google because your spelling was off? I get many hits for diazotization.
Here is a diazotizatoin test. Best of luck.
Harpoon - 23-11-2004 at 09:57
The procedure below can be carried out in about an hour. You'll need:
crushed ice
naphthalene-2-ol
concentrated hydrochloric acid
sodium carbonate
2 mol/l sodium hydroxide solution
sulphanilic acid, also called 4-aminobenzenesulphonic acid
sodium nitrite
Steps for the diazotisation of sulphanilic acid.
1. In a 100 ml beaker, stir 1.2 grams of sulphanilic acid into 7 ml distilled water, and add 2 mol/l sodium hydroxide solution in drops until the
mixture is just alkaline to universal indicator paper.
2. Add an equal volume of crushed ice, and then stir 2 ml concentrated hydrochloric acid to reprecipitate the sulphanilic acid.
3. In a boiling tube dissolve 0.5 grams of sodium nitrite in 5 ml distilled water. Cool in the ice bath.
4. Add the cooled sodium nitrite solution to the sulphanilic acid with stirring, whilst keeping the mixture in the ice bath. Diazotisation of the
sulphanilic acid will occur.
Optional steps for making the azodye naphthalene orange.
5. Warm 1 gram of naphthalene-2-ol with 4 ml of 2 mol/l sodium hydroxide solution and 10 ml of distilled water in a 100 ml beaker. Stir until it has
dissolved.
6. Stir in 0.5 grams of anhydrous sodium carbonate and cool in an ice bath
7. Add the diazotised sulphanilic acid to the ice-cold napthalen-2-ol. Stir during the addition, and continue to cool in ice.
8. Continue stirring for a few minutes. Napthalene orange should form.
[Edited on 23-11-2004 by Harpoon]
mordacious - 23-11-2004 at 10:37
thanks i did find one procedure to make methyl orange