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ChemicalBook CAS DataBase List o-Toluidine
95-53-4

o-Toluidine synthesis

14synthesis methods
The production of O-toluidine is based on the catalytic hydrogenation of O-nitrotoluene or the amination of toluene with methylhydroxylamine in the presence of aluminum trichloride (Windholz 1983). It is available as a technical grade with a minimum of 99.5% purity containing m-toluidine (0.4% maximum) and/or ptoluidine (0.1% maximum) as impurities (Anon. 1978). The stabilized technical grade may also contain less than 0.5% of unidentified stabilizing agents to prevent darkening.
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Yield:95-53-4 93%

Reaction Conditions:

with 2-(bis(4-methoxyphenyl)phosphanyl)-5-methylbenzenesulfonamide in tetrahydrofuran at 30; for 3 h;Inert atmosphere;Staudinger Azide Reduction;

Steps:

General Procedure A (for the substrates 1a-1m)

General procedure: Under a N2 atmosphere, the correspondingorganic azide (1.00 mmol, 1.0 equiv) was dissolved in anhydrous tetrahydrofuran(10 mL), followed by the addition of 2c (1.10 mmol, 1.1 equiv). The mixture was stirredat 30 C for 3 h. Upon completion, the mixture was concentrated in vacuo and the crudeproduct was purified by flash column chromatography.

References:

Li, Xingzhuo;Wang, Zhenguo;Luo, Wenjun;Wang, Zixu;Yin, Keshu;Li, Le [Molecules,2022,vol. 27,# 17,art. no. 5707]

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