Methanol → 4-Butyl-1,2-benzenediamine

1.11 g (5.15 mM) of 4-butyl-2-nitroaniline, 5 ml of methanol, 0.35 g of activated carbon and 0.04 gof ferric chloride hexahydrate were placed in a 50 ml-three-neckedflask and kept at about 60° C. To themixture, 1.5 ml (24.7 mM) of hydrazine hydrate wasgradually added dropwise, followed by stirring for 2 hours under heat refluxing. After the reaction, thereaction mixture was subjected to filtration by meansof suction under heating to remove the activatedcarbon. The filtrate was concentrated under reducedpressure and an appropriate amount of water was addedthereto. The mixture was subjected to extraction withethyl acetate. The organic layer was washed withwater and dried with milabilite, followed byconcentration under reduced pressure to obtain a crudeproduct. To the crude product (residue), anappropriate amount of hexane was added, followed bycooling on an ice bath to precipitate a crystal. Thecrystal was recovered by filtration to obtain 0.82 gof 4-butyl-1,2-phenylenediamine (Yield: 87.4%).

1. customkept at about 60° C
2. temperatureunder heat
3. temperaturerefluxing
4. customAfter the reaction
5. filtrationmixture was subjected to filtration by meansof suction
6. temperatureunder heating
7. customto remove the activatedcarbon
8. concentrationThe filtrate was concentrated under reducedpressure
9. extractionThe mixture was subjected to extraction withethyl acetate
10. washThe organic layer was washed withwater and
11. customdried with milabilite
12. customto obtain a crudeproduct
13. customfollowed bycooling on an ice bath
14. customto precipitate a crystal
15. filtrationThecrystal was recovered by filtration

ORD record

ord-975e32f40c474d50a250e28a28df7607

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05512209