Hydrochloric Acid → HCID 13721447, compound

A mixture of phenol (100 mg), ethyl 5-bromovalerate (222.2 mg), cesium carbonate (693 mg) and DMF (1.6 ml) was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was adjusted to pH 6 with 2N HCl solution. The aqueous phase extracted twice more with ethyl acetate. The combined organic phases were then washed with water and dried over sodium sulfate, and the solvent was removed in vacuo. The product obtained in this way was taken up in abs. ethanol (0.5 ml), 37.3 μl of hydrazine hydrate were added, and the mixture was heated under reflux for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was neutralized with 2N HCl solution. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were then washed with water and dried over sodium sulfate, and the solvent was removed in vacuo. The residue was purified by preparative HPLC. The product with the molecular weight of 208.11 (C11H16ClN2O2) was obtained in this way; MS (ESI): 209.1 (M+H+).

1. extractionThe aqueous phase extracted twice more with ethyl acetate
2. washThe combined organic phases were then washed with water
3. dry with materialdried over sodium sulfate
4. customthe solvent was removed in vacuo
5. customThe product obtained in this way
6. temperaturethe mixture was heated
7. temperatureunder reflux for 12 h
8. extractionThe aqueous phase was extracted twice with ethyl acetate
9. washThe combined organic phases were then washed with water
10. dry with materialdried over sodium sulfate
11. customthe solvent was removed in vacuo
12. customThe residue was purified by preparative HPLC
13. customThe product with the molecular weight of 208.11 (C11H16ClN2O2) was obtained in this way

ORD record

ord-371687e677374f158e29fe2011462be2

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07319108B2