59681-66-2

74-89-5

89-61-2

59681-66-2

1. 1,4-Dichloro-2-nitrobenzene (5 g, 26 mmol) was dissolved in an ethanol solution of 33% methylamine (20 mL), heated to 80 °C, and reacted for 15 hours. 2. After completion of the reaction, cooled to room temperature and removed the solvent under reduced pressure. 3. The crude product was used directly in the next step of the reaction. 4. Dissolve the crude product in ethanol (250 mL), add zinc powder (15 g), and slowly add 6N aqueous hydrochloric acid solution (40 mL) dropwise. 5. Stir the reaction for 3 hours at room temperature. 6. 6. After the reaction was completed, saturated sodium hydroxide solution was added slowly until the reaction solution became alkaline. 7. 7. Extract the aqueous layer with dichloromethane (3 x 100 mL). 8. 8. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. 9. The solvent was removed under pressure to afford the target product 4-chloro-N1-methylbenz-2-amine (1.7 g, 42% overall yield in two steps). 10. The product was analyzed by 1H NMR. 10. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 2.84 (s, 3H), 6.54 (d, J = 6.0 Hz, 1H), 6.70 (d, J = 3.0 Hz, 1H), 6.79 (dd, J = 3.0,6.0 Hz, 1H).