O-Toluidine acetylation

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

Acetyl-AT-metbyl-o toluidine. Acetyl-AT-metbyl-m-toluidine. Acetyl-AT-methyl-p-toluidine. Acetyl-A7-methyl-a-napbthylamine Acety 1-AT-metbyl- P-naphthy lamine... 

Acetyl- -methyl-o toluidine. Acetyl-jV-methyl-m-toluidine. Acetyl-jV-methyl-p-toluidine. Acetyl- -methyl- a-naphthylamine Acetyl-AT-methyl- p-naphthylamine... 

Boil a mixture of 10 g. (10 ml.) of o-toluidine and 38 g. (35 ml.) of acetic anhydride in a 75 or 100 ml. Claisen flask fitted with a reflux condenser (Fig. Ill, 28, 1, but with trap replaced by a calcium chloride or cotton wool guard tube) for 1 hour. Arrange the flask for distillation under reduced pressure (compare Fig. II, 20, 1) and distil acetic acid and the excess of acetic anhydride pass over first, followed by the diacetyl derivative at 152-153°/20 mm, some mono-acetyl-o-toluidine (1-2 g.) remains in the flask. The yield of diacetyl-o-toluidine is 14-15 g, it is a colourless, somewhat unstable hquid, which slowly sohdifies to yield crystals, m.p. 18°, To prepare the (mono-) acetyl-o-toluidine, warm a mixture of 5 g. 

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... 

To prepare the (mono-) acetyl-o-toluidine, warm a mixture of 5 g. 

The method of preparation adopted is substantially that of Buchka,- as this is the only one of practical value. w-Nitro-toluene has been obtained by a similar process from 5-nitro-2-aminotoluene (obtained by nitration of acetyl-o-toluidine), but this compound is not commercially available, and gives a poor product unless carefully purified. 

AcEIYLKETENE, 21, 64 Acetylsalicylyl chloride, 23, 66 Acetylsalicylyl peroxide, 23, 66 Acetyl-o-toluidine, 22, 94 substituted, conversion to indoles, 22, 95... 

Methylindole has been prepared, in very small yields, by distilling acetyl-o-toluidine with zinc dust,1 and in better yields by heating the toluidide with sodium ethoxide or with barium oxide in a current of hydrogen at 360-3800.2 The method described here has been used for the synthesis of substances related to physostigmine 3 and is a modification of Verley s procedure.4... 

Acetyl-o-toluidine, m.p. 110-111°, obtained from the Eastman Kodak Company, was used. After the reactants are introduced into the flask, they should be mixed thoroughly with a long spatula. 

The method described here is of general application to substituted acetyl- and benzoyl-o-toluidines. 

An interesting case of intramolecular azo coupling to an activated methyl group is the well-known synthesis of indazoles 72 starting from o-toluenediazonium salts 69 or from N-nitroso-N-acetyl-o-toluidine 67 . Recently the reaction mechanism (32) was elucidated When the reaction is run in the presence of D O or... 

DITHIZON see DWN200 DITHIZONE see DWN200 DITHRANOL, 10-ACETYL- see ACI640 DITHRANOL, 10-BUTYRYL- see BSY400 DITOIN see DNUOOO DITOINATE see DKQOOO 4,4 -DI-o-TOLUIDINE see TGJ750... 

Ninety grams (90.2 ml., 0.839 mole) of o-toluidine is slowly added to a mixture of 90 ml. of glacial acetic acid and 180 ml. (1.90 mole) of acetic anhydride contained in a 750-ml. twonecked flask equipped with a thermometer and a two-hole cork stopper for a gas inlet tube (Note 1). Acetylation occurs with evolution of heat. The mixture is cooled in an ice bath (Note 2) and nitrosated by rapid admission of a stream of nitrous gases (Note 3). The nitrous gases are obtained by the action of nitric... 

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