Ammonia → HCID 9942180, compound

Temperature

160 °C

A mixture of 2-bromo-4-ethylaniline (29.2 g) and cuprous cyanide (14.4 g) in dry pyridine (25.4 g) was stirred for 16 hours at 160° C. After cooling to 60° C., the resultant mixture was poured into a mixture (250 ml) of conc. aqueous ammonia and water (1:1) with stirring. To the resultant mixture was added ethyl acetate (300 ml) with stirring. Insoluble materials were filtered off. The organic layer was washed three times with water and with aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give an oily residue, to which was added benzene and concentrated under reduced pressure. These operations were repeated twice to remove pyridine. The resultant oily residue was subjected to a column chromatography using silica gel (developing solvent: a mixture of benzene and hexane (3:1)) to give 2-amino-4-ethylbenzonitrile (16.4 g).

1. temperatureAfter cooling to 60° C.
2. stirringwith stirring
3. stirringwith stirring
4. filtrationInsoluble materials were filtered off
5. washThe organic layer was washed three times with water
6. dry with materialwith aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customto give an oily residue
9. concentrationconcentrated under reduced pressure
10. customto remove pyridine
11. additiona mixture of benzene and hexane (3:1))

ORD record

ord-4fd5ebaa65ab48cea1f3a2fc1c876562

Source dataset

uspto-grants-1984_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04429126