4-Bromo-2-methylaniline → (4-bromo-2-methylphenyl)hydrazine

Temperature

80 °C

4-bromo-2-methylaniline (2.0 g) was dissolved in conc. HCl (10 mL) and heated to 80° C. for 30 minutes. The reaction was cooled to 5° C. and a solution of sodium nitrite (781.0 mg in 4.0 mL of water) was added over 10 minutes. The resulting mixture was then stirred at 5° C. for 30 minutes. A solution of tin(II)chloride (15.3 g in 8 mL of concentrated HCl) was added over 10 minutes, and the resulting solution was stirred at room temperature for 45 minutes. The reaction was made basic with 50% NaOH solution and a white precipitate formed. The solid was filtered and the filtrate extracted with dichloromethane. The organic extract was dried over magnesium sulfate, filtered and concentrated to yield 1.08 g (50%) of 1-(4-bromo-2-methylphenyl)hydrazine as a white solid. LC-MS @ 201.1 (M+1)

1. temperatureThe reaction was cooled to 5° C.
2. stirringthe resulting solution was stirred at room temperature for 45 minutes
3. customa white precipitate formed
4. filtrationThe solid was filtered
5. extractionthe filtrate extracted with dichloromethane
6. extractionThe organic extract
7. dry with materialwas dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-967a96cfeab841e1b539bd6d6e2726e0

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318762B2