3-Methoxy-4-methylaniline → (3-Methoxy-4-methylphenyl)hydrazine

Temperature

-5 °C

A stirred mixture of 100.0 g (0.73 mole) of 4-methyl-3-methoxyaniline in 800 mL of concentrated hydrochloric acid was cooled to -5° C. A solution of 501.5 g (0.73 mole) of sodium nitrite in 250 mL of water was added slowly while maintaining the temperature of the reaction mixture below 0° C. The resultant mixture was stirred at -5° C. for 30 minutes. A cold solution of 330.0 g (1.46 mole) of tin (II) chloride dihydrate in 360 mL of concentrated hydrochloric acid was added over one hour. After complete addition the resultant mixture was allowed to warm to room temperature. A solid precipitate formed and was collected by filtration and stirred in 200 mL of water. This mixture was neutralized with 50% aqueous sodium hydroxide, and extracted with toluene. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 58.0 g of 4-methyl-3-methoxyphenylhydrazine as an oil.

1. temperaturewhile maintaining the temperature of the reaction mixture below 0° C
2. temperatureto warm to room temperature
3. customA solid precipitate formed
4. filtrationwas collected by filtration
5. extractionextracted with toluene
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe filtrate was evaporated under reduced pressure

ORD record

ord-19cab3cc0f6c49cda0f8d0c42d5eff8a

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04806145