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ChemicalBook CAS DataBase List 3-Chloro-4-methylaniline
95-74-9

3-Chloro-4-methylaniline synthesis

11synthesis methods
-

Yield:95-74-9 83%

Reaction Conditions:

Stage #1:2-chloro-4-nitrotoluene with hydrogenchloride;1,1,1,3',3',3'-hexafluoro-propanol;iron in water at 20; for 0.5 h;
Stage #2: with sodium hydrogencarbonate in waterchemoselective reaction;

Steps:

2. General Procedure for the Reduction of Nitro Compounds
General procedure: The nitro compound (1 equiv), HFIP (10 equiv), Fe powder (5 equiv) were mixed in a tube. Then 2 N HCl aqueous solutions was added to the reaction mixture. After stirring at room temperature for 30 min, the reaction mixture was neutralized with sat. NaHCO3 (aq.) and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was then purified by column chromatography on silica gel to furnish the desired amine product.

References:

Chen, Xu-Ling;Ai, Bai-Ru;Dong, Yu;Zhang, Xiao-Mei;Wang, Ji-Yu [Tetrahedron Letters,2017,vol. 58,# 37,p. 3646 - 3649] Location in patent:supporting information

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