Ammonia → HCID 21812866, compound

To a solution of 4,4-dimethyl-3-oxo-pentanenitrile (22 g, 175.76 mmol) in 250 mL of ethanol is added ammonium nitrate (21 g; 263.64 mmol). The mixture is stirred under reflux overnight while ammonia gas is bubbled through the solution. The mixture is cooled to room temperature and diluted with 100 mL of water. The mixture is concentrated under reduced pressure to remove most of the ethanol. Aqueous sodium hydroxide (140 mL, 0.3N) is added and the mixture is extracted with ether (2×200 mL). The combined organic layers are washed with 50 mL of water, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford title compound. Assumed quantitative yield and used crude in subsequent reaction. ESI m/z 125=MH+

1. customis bubbled through the solution
2. additiondiluted with 100 mL of water
3. concentrationThe mixture is concentrated under reduced pressure
4. customto remove most of the ethanol
5. additionAqueous sodium hydroxide (140 mL, 0.3N) is added
6. extractionthe mixture is extracted with ether (2×200 mL)
7. washThe combined organic layers are washed with 50 mL of water
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-9b401d22cc864c1393346885c03ca814

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629157B2