108-44-1 m-Toluidine

TEST Aniline 0- toluidine m-> toluidine P-. toluidine I- naphthyl- amine 2- naphthyl- amine mono- methyl- aniline diphenyl- amine dimethyl- aniline triphenyl- amine... 

Water 2-methylpiperidine Water 3-metliylpipericline Water 4-methylpiperidine Water P picoline Water aa-Iutidine Glycerol m-toluidine. ... 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Acetyl-AT-methyl-o tolnidine Acetyl-AT-raethyl-m-toluidine. Acetyl-AT-methyl-p-toluldine. Acetyl-AT-methyl-a-naphthylam Ine Acety l- /-raethy 1- -naphthy lamlne... 

The preparation of 3-alkyl quinolines by traditional Skraup/Doebner-von Miller reaction typically results in very low yields. When ethylacrolein (9) is condensed with m-toluidine (8) under typical Skraup/Doebner-von Miller conditions, the yield of 10 is only 25%, compared to 65% with di-acetyl acetal 11. 

Aj Preparation of 5-Trifluoromethylaniline-2,4-Disulfonylchloride— H ml of chlorosulfonic acid Is cooled in an ice bath, and to the acid is added dropwise while stirring 26.6 grams of a,a,a-trifluoro-m-toluidine. 105 grams of sodium chloride is added during 1-2 hours, whereafter the temperature of the reaction mixture is raised slowly to 150°-160°C which temperature is maintained for three hours. After cooling the mixture, ice-cooled water is added, whereby 5-trifluoromethylaniline-2,4-disulfonyl chloride separates out from the mixture. 

Give the structures of the major organic products you would expect from reaction of m-toluidine (m-methylaniline) with the following reagents ... 

In each of two ordinary 250-cc. (8-oz.) narrow-mouthed bottles are placed 32.1 g. (32.5 cc., 0.3 mole) of m-toluidine and 33 (23 cc-y °-3 mole) of ethyl bromide (Note 1). The bottles are sealed with rubber stoppers wired tightly in place and then allowed to stand for twenty-four hours in a 2-1. beaker filled with water at room temperature (Note 2). The white crystalline mass in each bottle is broken up and the amine is liberated by shaking with 150 cc. of 10 per cent sodium hydroxide solution and 50 cc. of ether. The contents of the two flasks are combined, the lower aqueous layer is separated and discarded, and the ether solution of the amine is washed with 150 cc. of water, When the ether is distilled from a steam bath, the crude amine (90-92 g.) is obtained. 

A pure grade of m-toluidine was used. A practical grade of ethyl bromide gave satisfactory results. 

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