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 mixture 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 mixture 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-2c09d1244ae74f059fc05b66611d61f6

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353110B2