2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE Chemical Properties

Melting point:

>211°C (dec)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

CAS DataBase Reference

5425-81-0(CAS DataBase Reference)

2-AMINO-(4'-NITRO)ACETOPHENONE HYDROCHLORIDE Usage And Synthesis

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