Methylamines

Monomeihylamine, methylamine, CH3NH2-Colourless, inflammable gas with an ammo-niacal odour, very soluble in water, m.p. 

The solutions of all the methylamines in water are alkaline, but the alkalinity decreases with the number of methyl groups. 

In a more recent example, a shock-tube experiment was used to study the themial decomposition of methylamine between 1500 K and 2000 K [61, 62] ... 

Caution.—If the ethanol used to extract the methylamine hydrochloride is not absolute, i.e., if it contains traces of water, considerably less than the above suggested quantity will be required for the extraction, because the solubility of the hydrochloride will be markedly increased by the water present. The recrystallised material will now, however, contain traces of ammonium chloride. 

Methylamine evolved (fishy odour, alkaline reaction). 

The best method of drying the precipitate of methylamine hydrochloride is by centrifuging the Compound is hygroscopic. 

The absence of ammonium chloride and methylamine hydrochloride may be shown by the complete solubility of the product in chloroform. 

Pyrolysis of the methylamine salt (produced by neutralising mucic acid with aqueous methylamlne) in the presence of glycerol yields JV-methylpyrrole ... 

An ethereal solution of diazomethane is usually prepared immediately before it is required for reaction. Two intermediates may be used for this purpose, viz., nitrosomethylurea and p-tolylsulphonylmethylnitrosamide a number of methods are available for obtaining the former the latter is prepared from methylamine and p-toluenesulphonyl chloride. Nitrosomethylurea is not very stable at room temperatures and must be kept at 0° on the other hand p-tolylsulphonylmethylnitrosamide is a stable solid, which can be kept for long periods at room temperature in a dark bottle. 

An alternative method of preparation involves the interaction of methylamine hydrochloride with urea to give methylurea, followed by interaction with nitrous acid as above ... 

Tolylsulphonylmethylnitrosamide is obtained as follows. Interaction of p-toluenesulphonyl chloride and methylamine yields p toluenesulphonylmethyl amide ... 

In order to secure the maximum conversion of the methylamine into the sul-phonylmethylamide, the p-toluenesulphonyl chloride is introduced in several portions, and sodium hydroxide solution is added after each portion to liberate the methylamine from the hydrochloride formed in the reaction ... 

Determine the methylamine content of the commercial solution by titration with standard acid using methyl orange as indicator. Adjust the quantity of methyl-amine solution in accordance with the methylamine content for some commercial samples, the figure may be 33-40 per cent. 

Occasionally the liquid may not become acidic after the first or second addition, even through the sulphonyl chloride has reacted completely. (This is due to a smaller loss of methylamine than is expected.) If such is the case, no more than 5 minutes should be allowed between successive additions of sulphonyl cliloride and alkali. The whole procedure occupies about 30 minutes. 

Dimethylaminomethylindole (gramine). Cool 42 5 ml. of aqueous methylamine solution (5 2N ca. 25 per cent, w/v) contained in an 100 ml. flask in an ice bath, add 30 g. of cold acetic acid, followed by 17 -2 g. of cold, 37 per cent, aqueous formaldehyde solution. Pour the solution on to 23 -4 g. of indole use 10 ml. of water to rinse out the flask. Allow the mixture to warm up to room temperature, with occasional shaking as the indole dissolves. Keep the solution at 30-40° overnight and then pour it, with vigorous stirring, into a solution of 40 g. of potassium hydroxide in 300 ml. of water crystals separate. Cool in an ice bath for 2 hours, collect the crystalline solid by suction flltration, wash with three 50 ml. portions of cold water, and dry to constant weight at 50°. The yield of gramine is 34 g. this is quite suitable for conversion into 3-indoleacetic acid. The pure compound may be obtained by recrystaUisation from acetone-hexane m.p. 133-134°. 

Salts. Sodium benzoate Sodium benzenesulphonate Aniline hydrochloride Methylamine hydrochloride. 

METHOD 4 This here method was contributed by a scholar named Ritter. She is adamant about this method and considers it a major breakthrough. Ritter wants to do what was done in Method 2 except without the insidious methylamine. 

Who Needs Methylamine Anyway by Ritter, edited by The Professor... 

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