Acetic Acid → 4-Iodo-N1-methylbenzene-1,2-diamine

Temperature

70 °C

A mixture of an iron powder (1.7 g), acetic acid (2.2 ml), ethanol (80 ml), and water (25 ml) was stirred at 70° C. To the reaction mixture was added dropwise a mixture of (4-iodo-2-nitro-phenyl)-methyl-amine (2.0 g) and ethanol (20 ml). After that, the mixturee was stirred at 70° C. for 6 hours. Then, the reaction mixture was filtrated and thoroughly washed with THF. The resulting filtrate was concentrated under reduced pressure. To the resulting residue was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4-iodo-N1-methyl-benzene-1,2-diamine (1.6 g)

1. additionTo the reaction mixture was added dropwise
2. stirringAfter that, the mixturee was stirred at 70° C. for 6 hours
3. filtrationThen, the reaction mixture was filtrated
4. washthoroughly washed with THF
5. concentrationThe resulting filtrate was concentrated under reduced pressure
6. additionTo the resulting residue was poured saturated aqueous sodium hydrogen carbonate solution
7. extractionthe mixture was extracted with ethyl acetate
8. dry with materialThe organic layer was dried over sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-8e31494b2f79435f87da827da6172e50

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120823B2