Sulfuric Acid → Hexahydro-5-methyl-2H-azepin-2-one

Temperature

120 °C

4-methylcyclohexanone oxime in 5 mL 80% H2SO4 was added dropwise to H2SO4 (80%, 5 mL) while stirring and the reaction temperature was maintained at 120° C. with an external oil bath. An exotherm was observed. After 5 min, the reaction was removed from the oil bath and allowed to cool to room temperature. The reaction mixture was diluted with water (30 mL) and adjusted to pH 6 with concentrated NH4OH. This solution was further diluted with water (30 mL) and extracted with DCM (2×25 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product (1.6 g) was used for the next step without further purification.

1. customthe reaction was removed from the oil bath
2. temperatureto cool to room temperature
3. additionThe reaction mixture was diluted with water (30 mL)
4. additionThis solution was further diluted with water (30 mL)
5. extractionextracted with DCM (2×25 mL)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationAfter filtration and concentration
9. customthe crude product (1.6 g) was used for the next step without further purification

ORD record

ord-c8efe22267f94f1d8121288ad77b2322

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772301B2