Acetone → HCID 58494898, compound

To a suspension of 32.94 g of 2,2′-(3-chloro-1,2-phenylene)diacetonitrile in 100 ml of acetic acid was added dropwise 100 ml of a 33% hydrogen bromide-acetic acid solution over 1.5 hours while keeping the inner temperature at 20° C. or lower. The reaction mixture was stirred at room temperature for 3 hours, and then to the reaction mixture were added diethylether and acetone. The resulting candy-like dark brown solid substance and the suspension were separated, the suspension was concentrated under reduced pressure, and the candy-like substance was pulverized in acetone to obtain a suspension. The concentrated residue and the acetone suspension were combined and concentrated under reduced pressure, and to the residue was added EtOAc, followed by stirring. The solid was collected by filtration. The resulting solid was suspended in 400 ml of water which had been heated to 80° C., and 31.2 g of sodium acetate was added thereto, followed by stirring at 90° C. for 3 hours. The reaction mixture was cooled to room temperature and then the solid was collected by filtration to obtain 22.506 g of 6-chloro-1H-3-benzazepine-2,4(3H,5H)-dione as a brown solid.

1. customat 20° C.
2. customThe resulting candy-like dark brown solid substance and the suspension were separated
3. concentrationthe suspension was concentrated under reduced pressure
4. customto obtain a suspension
5. concentrationconcentrated under reduced pressure
6. additionto the residue was added EtOAc
7. stirringby stirring
8. filtrationThe solid was collected by filtration
9. temperaturehad been heated to 80° C.
10. addition31.2 g of sodium acetate was added
11. stirringby stirring at 90° C. for 3 hours
12. temperatureThe reaction mixture was cooled to room temperature
13. filtrationthe solid was collected by filtration

ORD record

ord-db04749ce37f49a8a4865b9b2909b93d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108977B2