N1-(4-ACETYL-3-HYDROXYPHENYL)ACETAMIDE

N1-(4-ACETYL-3-HYDROXYPHENYL)ACETAMIDE Property

Melting point:

141-142℃

Boiling point:

419.0±35.0 °C(Predicted)

Density 

1.267

storage temp. 

Sealed in dry,Room Temperature

pka

9.70±0.10(Predicted)

Appearance

Light brown to off-white Solid

Safety

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

N1-(4-ACETYL-3-HYDROXYPHENYL)ACETAMIDE Chemical Properties,Usage,Production

Synthesis

Step 2: Preparation of 4-acetamido-2-hydroxyacetophenone N-(4-acetyl-3-hydroxyphenyl)acetamide was prepared based on the improved method of Elliott, J.M. et al. (J. Med. Chem., 1992, 35, 3973-3976): over 20 min, aluminum chloride (27 g, 206 mmol) was added batchwise to mechanically stirred 3'-methoxyacetanilide (10 g, 60.5 mmol), acetyl chloride (12.5 mL, 175.6 mmol) and dichloromethane (25 mL) mixture. Upon completion of the reaction, all dichloromethane was removed by distillation and the resulting viscous mixture was left to heat at 80°C for 3.5 hours. Subsequently, chlorobenzene (60 mL) was added and the mixture was heated to reflux (132°C) and stirred under reflux conditions for 1 hour. The reaction mixture was cooled to 0°C and crushed ice was slowly added while stirring. The resulting solid product was collected by filtration and purified by silica gel column chromatography to afford N-(4-acetyl-3-hydroxyphenyl)acetamide 7.34 g (63% yield). 1H NMR (400 MHz, DMSO-d6): δ 12.31 (s, 1H), 10.26 (s, 1H), 7.83 (d, J = 8.8 Hz, 1H), 7.34 (d, J = 1.8 Hz, 1H), 7.05 (dd, J = 8.8, 1.8 Hz, 1H), 2.56 (s, 3H), 2.08 (s, 3H) . MS-APCI (m/z +): 194 (M + 1).

References

[1] Patent: WO2007/88438, 2007, A2. Location in patent: Page/Page column 17
[2] Journal of the Chemical Society, 1958, p. 146,149
[3] Journal of the Chemical Society, 1931, p. 2388,2406
[4] Bulletin de la Societe Chimique de France, 1952, p. 639
[5] Patent: US5622989, 1997, A