3-Chloro-4-methylaniline synthesis
- Product Name:3-Chloro-4-methylaniline
- CAS Number:95-74-9
- Molecular formula:C7H8ClN
- Molecular Weight:141.6
121-86-8
95-74-9
General procedure for the synthesis of 3-chloro-p-toluidine from 2-chloro-4-nitrotoluene: General method: Nitro compounds (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, a 2N aqueous hydrochloric acid solution was slowly added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3) solution. Next, it was extracted three times with saturated aqueous sodium bicarbonate solution. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to obtain the target product 3-chloro-p-toluidine.
121-86-8
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95-74-9
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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
89794-02-5
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7006-52-2
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99-99-0
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95-74-9
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95-74-9
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