Ammonium Chloride → 3-Iodo-4-methoxyaniline

To 2-iodo-1-methoxy-4-nitrobenzene (485 mg, 1.74 mmol) suspended in methanol (6 mL) a solution of NH4Cl (465 mg, 8.69 mmol) in water (4.9 mL) and powdered Fe (290 mg, 5.192 mmol) were added and the mixture was heated to reflux for 3 h. The precipitate formed was filtered off and the filtrate was evaporated until the methanol was eliminated. After diluting with water and alkalinization with sodium carbonate the mixture was extracted with EtOAc (4×20 mL). The combined organic extracts were washed with brine (3×10 mL), water (10 mL), dried over sodium sulfate and the solvent was removed under vacuum. The crude dark oil was purified by flash chromatography on silica gel (hexane/EtOAc 1/1) to afford 400 mg of solid that was crystallized from n-pentane and diethyl ether to yield the title compound (363 mg, 83%).

1. additionwere added
2. temperaturethe mixture was heated
3. temperatureto reflux for 3 h
4. customThe precipitate formed
5. filtrationwas filtered off
6. customthe filtrate was evaporated until the methanol
7. additionAfter diluting with water and alkalinization with sodium carbonate the mixture
8. extractionwas extracted with EtOAc (4×20 mL)
9. washThe combined organic extracts were washed with brine (3×10 mL), water (10 mL)
10. dry with materialdried over sodium sulfate
11. customthe solvent was removed under vacuum
12. customThe crude dark oil was purified by flash chromatography on silica gel (hexane/EtOAc 1/1)

ORD record

ord-6acd3cc46ddd433fb5a8d77c07c705a4

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912200B2