Download our new 2011 product
catalog online: |
 PDF file |  Excel file | SDF file |
|
|
| Typical applications of Bredereck's reagent（CAS:5815-08-7）（16） |
| 2022-06-21 |
|
|
1、
A solution of 2-methyl-1-nitronaphthalane (5.00 g, 26.7 mmol)
and tert- butoxybis(dimethylamino)methane（CAS:5815-08-7） (8.27 g, 40.1 mmol) in 10 mL of toluene was refluxed at 120 °C for 15 h.
Additional ter/-butoxybis(dimethylamino)methane (3.76 g, 13.4 mmol) was added and the reaction was refluxed at 120 °C for another 24 h.
The mixture was cooled to rt and 50 mL of hexanes was added. After vigorously stirring for 30 min, a brick red solid was collected,
washed with additional hexanes, and dried to provide (E)-N, N-dimethyl-2-(l-nitro-2- naphthyl)etliylenamine that gave proton NMR spectra consistent with theory.
2、
To a solution of the above compound (10.0 g, 41.3 mmol) and potassium carbonate (13.7 g, 99.0 mmol) in 300 mL of 1 :1 ?-BuOH:H2O was added potassium permanganate (15.7 g, 99.0 mmol) slowly over 30 min.
The reaction mixture was stirred at rt for 17 h, and a black precipitate was filtered and washed twice with 100 mL of water.
The filtrate was concentrated to 200 mL in volume, and acidified with 6 N HCl to pH ~2. A beige precipitate was collected, washed twice with 100 mL of water, and dried to provide l-nitro-2-naphthoic acid that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 218.1 for [M+H]+.
Ref：[ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 652 - 656]
|
|
