Ammonium Chloride → HCID 23152864, compound

Temperature

70 °C

To a solution of 1-iodo-4-methyl-2-nitrobenzene (5.00 g, 19 mmol) in tetrahydrofuran (12.5 ml), methanol (25 ml) and water (6.3 ml) were added reduced iron (5.30 g, 95 mmol) and ammonium chloride (6.10 g, 114 mmol), and the mixture was stirred overnight at 70° C. The reaction mixture was allowed to cool to room temperature, tetrahydrofuran (50 ml) was added to the reaction mixture. After filtration through celite, the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (20 ml) was added 4N HCl-ethyl acetate solution (10 ml). The precipitated solid was collected by filtration, washed with ethyl acetate, and dried in vacuo to give 2-iodo-5-methylphenylamine hydrochloride (2.56 g, yield 50%).

1. temperatureto cool to room temperature
2. filtrationAfter filtration through celite
3. concentrationthe filtrate was concentrated under reduced pressure
4. additionWater was added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationAfter filtration
9. customthe solvent was evaporated under reduced pressure
10. additionTo a solution of the residue in ethyl acetate (20 ml) was added 4N HCl-ethyl acetate solution (10 ml)
11. filtrationThe precipitated solid was collected by filtration
12. washwashed with ethyl acetate
13. customdried in vacuo

ORD record

ord-dc416d4f418a4b4abf9d612b1a1ad6b7

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977331B1