3-Methoxyaniline → (3-Methoxyphenyl)hydrazine

Temperature

0 °C

A stirred solution of 50.0 g (0.41 mole) of 3-methoxyaniline in 60 mL of concentrated sulfuric acid and 100 mL of water was cooled to -5° C., and a solution of 28.0 g (0.41 mole) of sodium nitrite in water was added slowly while maintaining the temperature of the reaction mixture below 0° C. The mixture was stirred at 0° C. for 1 hour, then added slowly to a chilled, stirred solution of 100 g (0.44 mole) of stannous chloride dihydrate in 300 mL of concentrated hydrochloric acid. After complete addition, the reaction mixture was allowed to warm to ambient temperature and stand for 16 hours. The reaction mixture was filtered and the filter cake made basic. The basic material was extracted with diethyl ether. The reaction mixture filtrate was also made basic and extracted with diethyl ether. The ether extracts were combined and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to give 49.1 g of product as an oil.

1. temperaturewhile maintaining the temperature of the reaction mixture below 0° C
2. additionadded slowly to a chilled
3. additionAfter complete addition
4. temperatureto warm to ambient temperature
5. waitstand for 16 hours
6. filtrationThe reaction mixture was filtered
7. extractionThe basic material was extracted with diethyl ether
8. extractionextracted with diethyl ether
9. dry with materialdried with magnesium sulfate
10. filtrationThe mixture was filtered
11. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-1e71d296711047dd99cb5a4510df69f4

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04705557