5- Nitro-2-toluidine

Nitro-/w-toluic acid, m331 6-Nitro-/n-toluic acid, m337 2-Nitro-/ -toluidine, m330 4-Nitro-o-toluidine, m328... 

To 500 g. of 95 per cent ethyl alcohol in a 5-I. flask are added 1.70 g. of m-nitro- -toluidine (3-nitro-4-aminotoluene, m. p. 112-1140, Note r) and 250 g. of concentrated sulfuric acid. The solution is chilled to ro° by means of an ice bath, and a solution of 85 g. of technical sodium nitrite in a minimum quantity of water is slowly added, with stirring, the temperature being kept below to0. The mixture is now warmed very gently on the water bath under an efficient reflux condenser (from the upper end of which a tube leads to a hood or through water) until evolution of gas ceases (Note 2). The alcohol and aldehyde are then carefully distilled off, using a fractionating column and heating in an oil or brine bath (Note 3) when the temperature of the vapors reaches 8o° fractionation is stopped and the residue is distilled in a current of steam. The oil is separated from the distillate and the aqueous portion shaken out once with r5o-200 cc. of benzene. The united oil and extract are dried with a... 

Nitroso-d-naphthol, II, 61-62 Nitroso- 3-phenylhydroxylamine, IV, 21 w-Nitrotoluene, III, 91-93 -Nitrotoluene, II, 53 iw-Nitro- -toluidine, III, 91 Nitrous anhydride, IV, 27... 

Alternatively, the procedure of example 10 may be followed after the nitro-toluidine is in the paste form. 

Dinitroaniline iV-Methyl-2-nitroaniline A-Ethyl-3-nitroaniline iV-Methyl-3-nitro-/ -toluidine A-Methyl-4-nitroaniline A-Ethyl-4-nitroaniline A-Isopropyl-4-nitroaniline A-Ethyl-3-methyl-4-nitroaniline iV -Dimethyl -nitroaniline... 

Uses. (9-Nitrotoluene is used in the synthesis of intermediates for azo dyes, sulfur dyes, mbber chemicals, and agriculture chemicals. Typical intermediates are o-toluidine, o-nitrobenzaldehyde, 2-nitro-4-chlorotoluene, 2-nitro-6-chlorotoluene, 2-amino-4-chlorotoluene (Fast Scarlet TR Base), and 2-amino-6-chlorotoluene (Fast Red KB Base). -Nitrotoluene is used principally in the production of intermediates for azo and sulfur dyes. Typical intermediates are -toluidine, -nitrobenzaldehyde, and 4-nitro-2-chlorotoluene. 

Important analogs of aniline include the toluidines, xyUdines, anisidines, phenetidines, and its chloro-, nitro-. A/-acetyl. A/-alkyl. A/-aryl. A/-acyl, and sulfonic acid derivatives. 

Catalytic hydtogenation is the most efficient method for the large scale manufacture of many aromatic and ahphatic amines. Some of the commercially important amines produced by catalytic hydrogenation include aniline (from nitrobenzene), 1,6-hexanediamine (from adiponitrile), isophoronediamine (from 3-nitro-l,5,5-trimethylcyclohexanecarbonitrile), phenylenediamine (from dinitrobenzene), toluenediamine (from dinitrotoluene), toluidine (from nitrotoluene), and xyhdine (from nitroxylene). As these examples suggest, aromatic amines ate usually made by hydrogenating the... 

Nitric acid, 98 Nitric oxide, 98 Nitrilotriacetic acid, 98 p-Nitroaiiiline, 99 Nitrobenzene, 99 Nitrocarbono SA, 146 Nitrocellulose, 99 p-Nitrochlorobenzene, 99 Nitroethane, 99 Nitrofen, 99 Nitrogen, 99 Nitrogen dioxide, 99 Nitrogen oxides, 99 Nitrogen trifluoride, 99 Nitroglycerin, 100 Nitrokemia 200 Rt., 167 Nitromethane, 100 5-Nitro-o-anisidine, 99 5-Nitro-o-toluidine, 100 Nitrophenols, 100... 

In this method the nitro group in the aliphatic nitro compound is usually present on a carbon atom, which is also activated by CO-functioiiality (aldehyde, ester, arylketoiie). A successful application of this method is the Borsche modification of the Friedlander synthesis, involving condensation of A-(3-amino-4-picolylidene)-p-toluidine (17) with [Pg.289]

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