Tin tetrachloride → (4-Chloro-3-Methoxy-phenyl)-hydrazine

Temperature

0 °C

Concentrated hydrochloric acid (12 mL) and a solution of sodium nitrite (1.7 g, 24.4 mmol) in water (8 mL) were added to a solution of 4-chloro-3-methoxy aniline (3.86 g, 24.4 mmol) in water (8 mL), at −10° C. The mixture was stirred for 30 minutes and was then added to solution of tin chloride (14.89 g, 66 mmol) in concentrated hydrochloric acid (24 mL) and water (24 mL), cooled to 0° C. The reaction mixture was stirred for 18 hours, allowing the temperature to rise to 25° C. The resulting precipitate was filtered off and the solid was re-crystallised from heptanes/ethyl acetate (33:66) to afford the title compound the title compound as white solid in 72% yield, 3 g

1. stirringThe reaction mixture was stirred for 18 hours
2. customto rise to 25° C
3. filtrationThe resulting precipitate was filtered off
4. customthe solid was re-crystallised from heptanes/ethyl acetate (33:66)

ORD record

ord-d836384d371549f6ae742164692af9d8

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511057B2