Methanol → 2-Methyl-2-(4-nitrophenyl)propan-1-amine

To a mixture of the compound (152 mg) obtained in Example 179, methanol (10 ml) and chloroform (10 ml), hydrazine monohydrate (0.05 ml) was added and heated under reflux for 24 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; following addition of 2 N HCl, the mixture was washed with ethyl acetate. Then, the aqueous layer was made alkaline with a 2 N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 71 mg of the titled compound (yield, 78%).

1. additionwas added
2. temperatureheated
3. temperatureunder reflux for 24 h
4. filtrationThe reaction mixture was filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionaddition of 2 N HCl
7. washthe mixture was washed with ethyl acetate
8. extractionextracted with ethyl acetate
9. washThe organic layer was washed with a saturated aqueous sodium chloride solution
10. dry with materialdried with anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure

ORD record

ord-0a4c13141f554341a2a3e177ecc32363

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06534546B1