Hydrazine hydrate (1:1) → HCID 178434515, compound

Temperature

90 °C

To 4-bromophenylacetone (5.0 g, 23.5 mmol, 1.0 equiv) (Acros Organics 34216) was added N,N-dimethylformamide dimethyl acetal (11.3 ml, 84.6 mmol, 3.6 equiv) and the mixture was heated to 90° C. for 6 hours. The solvents were removed and the resulting gum was dissolved in ethanol (235 ml) with additional heating. Hydrazine hydrate (1.37 ml, 28.2 mmol, 1.2 equiv) was added and the mixture was heated to reflux for 15 hours. The solvents were removed under reduced pressure and the solid was triturated with dichloromethane to afford the title compound, 2.24 g (40%); LCMS (PS-A) Rt 2.87 min [M+H]+ 238. Further material could be isolated from the mother liquor.

1. customThe solvents were removed
2. dissolutionthe resulting gum was dissolved in ethanol (235 ml) with additional heating
3. temperaturethe mixture was heated
4. temperatureto reflux for 15 hours
5. customThe solvents were removed under reduced pressure
6. customthe solid was triturated with dichloromethane

ORD record

ord-1fe364fba7d24825a4138458c5e119cb

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691806B2