| Identification | More | [Name]
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE | [CAS]
5425-81-0 | [Synonyms]
AURORA 23208
OTAVA-BB BB7110952478
2-AMino-p-nitro-acetophenone HCl
2-AMino-4'-nitroacetophenone HCl
2-AMINO-P-NITRO-ACETOPHENONE HYDROCHLORIDE
2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE
2-AMINO-1-(4-NITRO-PHENYL)-ETHANONE HYDROCHLORIDE
2-Amino-1-(4-nitrophenyl)ethanone hydrochloride (1:1)
Ethanone, 2-amino-1-(4-nitrophenyl)-, hydrochloride (1:1) | [Molecular Formula]
C8H9ClN2O3 | [MDL Number]
MFCD00025591 | [Molecular Weight]
216.62 | [MOL File]
5425-81-0.mol |
| Hazard Information | Back Directory | [Synthesis]
Example 2: Synthesis of 2-amino-1-(4-nitrophenyl)ethanone hydrochloride
2-Bromo-4'-nitroacetophenone (25 g) prepared in Example 1 was dissolved in dichloromethane (250 mL), hexamethylenetetramine (20.1 g) was added, and the reaction was stirred for 1 hour at room temperature. After the reaction was completed, the solid crude product (30 g) was collected by filtration. The crude product was dissolved in a mixture of ethanol (162 mL) and concentrated hydrochloric acid (40 mL) and the reaction was continued with stirring for about 3 hours. After the reaction mixture was left to stand for about 48 hours, the solid product was precipitated, filtered, washed with water and dried to give the target compound 2-amino-1-(4-nitrophenyl)ethanone hydrochloride (refer to the method described in US4812470).
Yield: 11.8 g (72% yield);
1H NMR (DMSO-d6, 300MHz): δ 8.3 (broad peak, 3H), 8.38 (double peak, 2H), 8.27 (double peak, 2H), 4.68 (single peak, 2H). | [References]
[1] Patent: WO2011/55289, 2011, A2. Location in patent: Page/Page column 36
[2] Patent: WO2012/29032, 2012, A2. Location in patent: Example 2
[3] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 324 - 342
[4] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 203 - 215
[5] Journal of Medicinal Chemistry, 1982, vol. 25, # 9, p. 1045 - 1050 |
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