5-Iodo-2-methylaniline

41252-97-5

83863-33-6

The general procedure for the synthesis of 5-iodo-2-methylaniline from 4-iodo-2-nitrotoluene was as follows: to a 300 mL ethanol solution of 4-iodo-1-methyl-2-nitrobenzene (25.0 g, 107 mmol) was added platinum sulfide (3.00 g) and ammonium formate (20.3 g, 321 mmol). The reaction mixture was heated to reflux and maintained for 12 hours. Upon completion of the reaction, the mixture was cooled to 22 °C and filtered through a Celite pad to remove solid impurities. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was diluted with 300 mL of water and subsequently extracted with dichloromethane (3 x 200 mL). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. Finally, the organic phase was concentrated under reduced pressure to afford the target product 5-iodo-2-methylaniline (21.1 g, 95% yield). Mass spectrometry analysis showed MS m/z = 234 (M + H).