Sodium Diformylamide → Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Temperature

70 °C

At RT, 411 mg (4.33 mmol) of sodium diformylamide were added to 1.0 g (3.73 mmol) of 2-bromo-1-(2,3-dichlorophenyl)ethanone [for the preparation, see for example U.S. Pat. No. 5,831,132] in 4 ml of acetonitrile, and the mixture was stirred at RT overnight. The mixture was then heated to 70° C. and filtered whilst still warm. The solid that remained was washed with 2 ml of hot acetonitrile. The combined filtrates were freed from the solvent on a rotary evaporator. 10 ml of a 5% strength ethanolic hydrogen chloride solution were added to the dark-brown oily residue, and the mixture was stirred at RT overnight. The volatile components were removed on a rotary evaporator and the yellow solid that remained was stirred in 20 ml of boiling diethyl ether. After cooling to RT, the solid was isolated by filtration, washed with diethyl ether and dried under high vacuum. This gave 410 mg (46% of theory) of the title compound.

1. customfor the preparation
2. filtrationfiltered
3. temperaturewhilst still warm
4. washThe solid that remained was washed with 2 ml of hot acetonitrile
5. customThe combined filtrates were freed from the solvent on a rotary evaporator
6. addition10 ml of a 5% strength ethanolic hydrogen chloride solution were added to the dark-brown oily residue
7. customThe volatile components were removed on a rotary evaporator
8. stirringthe yellow solid that remained was stirred in 20 ml of boiling diethyl ether
9. temperatureAfter cooling to RT
10. customthe solid was isolated by filtration
11. washwashed with diethyl ether
12. customdried under high vacuum

ORD record

ord-fd54a25ebf8f4137826fd17b9db92513

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09180120B2