Hydrochloric Acid → 4-Chloro-3-(cyclopropylmethoxy)aniline

Temperature

80 °C

1-chloro-2-cyclopropylmethoxy-4-nitro-benzene (2.3 g, 10 mmol) was dissolved in ethanol (30 ml) and water (30 ml), and then sodium dithionite was gradually added thereto. This was stirred at 80° C. for four and half hours. After cooling it to room temperature, an aqueous solution of 5 M hydrochloride (40 ml) was added to the reaction mixture. This was stirred at room temperature for one hour. Then, an aqueous solution (42 ml) of 5 M sodium hydroxide was added, and the solution was alkalinized and extracted with ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 4-chloro-3-cyclopropylmethoxy-phenylamine was obtained as a pale yellow gum-like material (1.4 g).

1. temperatureAfter cooling it to room temperature
2. stirringThis was stirred at room temperature for one hour
3. extractionextracted with ethyl acetate
4. washThe extract was washed with water
5. dry with materialan aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
6. customThe desiccant was removed by filtration, and concentration
7. customThen, the residue obtained by concentration under reduced pressure
8. customwas purified by silica gel column chromatography

ORD record

ord-ce2c6beb2e6148daa545551708f84bd6

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829199B2