Acetic Acid → HCID 178438048, compound

Temperature

140 °C

A mixture of 2-(4-bromo-benzyl)-3-oxo-pentanenitrile (1, 10.4 g, 39.1 mmol) and hydrazine hydrate (1.9 ml, 39.1 mmol) in 35 ml of a 1:1 mixture of ethanol and acetic acid was heated in a microwave reactor to 140° C. for 15 min. After cooling the reaction mixture was diluted with ethyl acetate and washed several times with sat. sodium bicarbonate, followed by brine. The organic layer was dried over Na2 SO4 and evaporated to give a mixture of 2 and its N-acetamide. For conversion of the latter to 2, the crude product was taken up in 1N sodium hydroxide and heated to 160° C. in a microwave reactor until no N-acetamide could be detected by LC-MS (10-20 min). The reaction mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over Na2 SO4 and evaporated to yield 2 as a white powder, which was used in the next step without further purification.

1. temperatureAfter cooling the reaction mixture
2. washwashed several times with sat. sodium bicarbonate
3. customThe organic layer was dried over Na2 SO4
4. customevaporated
5. customto give
6. customcould be detected by LC-MS (10-20 min)
7. extractionThe reaction mixture was extracted with ethyl acetate
8. washthe organic layer was washed with brine
9. customdried over Na2 SO4
10. customevaporated

ORD record

ord-f7be672f5e1e4570a4ade7ff1399c86d

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748435B2