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-daa8d2bb0c494e3e881aa52790730fcc

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076356B2