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ChemicalBook CAS DataBase List 2-Methyl-4-nitroaniline

2-Methyl-4-nitroaniline synthesis

10synthesis methods
N-Benzenesulfonyl-o-toluidine is dissolved in chlorobenzene at 40 – 50 ℃, and 62 % nitric acid is added gradually to give 5- nitro-N-benzenesulfonyl-o-toluidine, which is isolated and hydrolyzed in sulfuric acid to give 5-nitro-o-toluidine in 80 % yield.
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Yield:99-52-5 55.9%

Reaction Conditions:

Stage #1:o-toluidine with acetic anhydride;acetic acid at 140; for 4.2 h;
Stage #2: with nitric acid; pH=7 for 5 h;
Stage #3: with sulfuric acid; pH=7 for 3 h;

Steps:

1 Example 1
In a 250 ml reaction bottle, put 100 g of glacial acetic acid and 25.5 g of acetic anhydride.10.7 g of o-toluidine was added dropwise, the temperature was raised to 140 ° C, and the reaction was carried out for 4.2 hours.Add 11g of nitric acid for cooling, react for 5 hours, add purified water,Adjust pH = 7 with liquid alkali, precipitate solid, suction filter, stir the filter cake with water,Add 60g of concentrated sulfuric acid dropwise, hold for 3 hours, cool down, add liquid alkali to adjust pH = 7,Precipitate the solid and dry to obtain 8.5 g of product, yield 55.9%Melting point is 127.3 ~ 128 ° C.

References:

Wang Xiaoqiao;Wang Cunliang;Xu Lingyan;Yan Xuewen;Huang Huanjun CN110642723, 2020, A Location in patent:Paragraph 0008

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