HCID 58056182, compound → HCID 26189280, compound

Stannous chloride (1.04 g, 5.49 mmol) was added to a solution of 4-chloro-1-(3-methoxy-propoxy)-2-nitro-benzene (0.448 g, 1.82 mmol) in a mixture of ethanol and ethyl acetate (1/1, 20 mL) and the resulting mixture was stirred at room temperature overnight. More stannous chloride (0.76 g, 4 mmol) was added and the reaction mixture was stirred for 1 day. The resulting mixture was partitioned between an aqueous solution of sodium bicarbonate (5%) and ethyl acetate, the aqueous solution was separated and extracted twice with ethyl acetate, the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The yellow oily residue was purified by flash chromatography (hexane/EtOAc, 80/20 to 60/40) to give 0.29 g (74% yield) of 5-chloro-2-(3-methoxy-propoxy)-phenylamine as a yellow oil.

1. stirringthe reaction mixture was stirred for 1 day
2. customThe resulting mixture was partitioned between an aqueous solution of sodium bicarbonate (5%) and ethyl acetate
3. customthe aqueous solution was separated
4. extractionextracted twice with ethyl acetate
5. washthe combined organic extracts were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe yellow oily residue was purified by flash chromatography (hexane/EtOAc, 80/20 to 60/40)

ORD record

ord-08b680f1a60a4dcf8dda4d744bdd38a3

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2