2,6-Dinitrophenyl methyl ether → 1,3-Benzenediamine, 2-methoxy-

Temperature

70 °C

A 2 L round bottomed flask was charged with 23 g (116 mmol) 2-methoxy-1,3-dinitrobenzene and 261 g (1.16 mol) tin chloride dihydrate. 160 mL EtOH was added, and the resulting suspension was stirred at 70° C. for 90 min. In the beginning, the reaction is very exothermic be careful! The solvent was removed and the reaction mixture was diluted with H2O and slowly added to about 500 mL of a 10 M NaOH solution. The suspension was cooled down to RT and extracted three times with EtOAc. The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The product was obtained as red oil and used without further purification.

1. customThe solvent was removed
2. additionthe reaction mixture was diluted with H2O
3. additionslowly added to about 500 mL of a 10 M NaOH solution
4. temperatureThe suspension was cooled down to RT
5. extractionextracted three times with EtOAc
6. dry with materialThe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customThe product was obtained as red oil
10. customused without further purification

ORD record

ord-48a6c34d80df4965ac7dec896a4c0460

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206211B2