Acetyl-p-toluidine

Acetyl-o-toluidine Acetyl-m-tolnidine Acetyl-p-toluidine... 

This is readily prepared by nitration of /V-acetyl-p-toluidine followed by alkaline hydrolysis to remove... 

SYNS p-ACETAMIDOTOLUENE p-ACETO-TOLUIDE 4-ACETOTOLUIDE 4-(ACETYL-AMINO)TOLUENE N-ACETYL-p-TOLUIDIDE ACETYL-p-TOLUIDINE p-METHYLACETANILIDE 4-METHYLACETANILIDE 4 -METHYLACETANILIDE... 

A solution of 60 g (0.57 mole) of sodium chlorate in 70 ml, of water is added slowly with stirring at 5° to a solution of 200 g. (1.35 moles) of acetyl-p-toluidine in 400 ml. of acetic acid and 600 ml. of concentrated hydrochloric acid. The mixture is stirred for 30 minutes, 400 ml. of additional concentrated hydrochloric acid is added, and the mixture is refluxed 2 hours and steam-distilled to remove the acetic acid and some oily material. The residual solution is then made alkaline and steam-distilled to remove the amine. The amine is extracted from the distillate with ether, and the ethereal solution is distilled to give 225 g. (60%) of 3-chloro-4-aminotoluene boiling at 220-225°. The product contains small amounts of p-toluidine and dichloro-p-toluidine. 

Derivation From acetyl-p-toluidine by nitration. Hazard Toxic by ingestion. 

Chlorination, acenaphthene, 69 acetophenone, 71 acetyl-p-toluidine, 72 anthranilic acid, 8 p-chlorotoluene in side chain, 74 8-ethylisothiuronium sulfate, 142 2-methylnaphthalene, 79 succinimide, 86 with NaClOs and HC1, 72 with sulfuryl chloride, 8 Chloromethylation, ethylbenzene, 146 p-xylene, 129 thiophene, 80... 

When groups such as hydroxyl or amino that are sensitive to oxidation are present as well as an alkyl group, then oxidation of the latter is seldom a smooth reaction. Amino groups can be acetylated, so that, for example, p-(acetylamino)benzoic acid is obtained from A-acetyl-p-toluidine by permanganate 404 anthranilic acid can be derived similarly from A-acetyl-o-toluidine. In such cases it is best to keep the reaction mixture neutral by adding magnesium sulfate. 

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