N-(4-methylcyclohexylidene)hydroxylamine

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. the reaction was removed from the oil bath to cool to room temperature The reaction mixture was diluted with water (30 mL) This solution was further diluted with water (30 mL) 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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Methylcyclohexanone (2.0 g, 17.8 mmol) was mixed with hydroxylamine hydrochloride (1.86 g, 26.8 mmol) and sodium acetate (2.63 g, 32.0 mmol) in a mixture of EtOH (20 mL) and water (12 mL). The mixture was refluxed for 5 h. All solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. After separation, the organic layer was washed with brine, dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was used for the next step without further purification. The mixture was refluxed for 5 h All solvent was removed under reduced pressure the residue was partitioned between ethyl acetate and water After separation the organic layer was washed with brine dried over anhydrous sodium sulfate After filtration and concentration the crude product was used for the next step without further purification