2-Methyl-3-nitrophenylacetic Acid Chemical Properties

Melting point:

132-136 °C

Boiling point:

377.6±27.0 °C(Predicted)

Density 

1.346±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Solid

pka

4.05±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C9H9NO4/c1-6-7(5-9(11)12)3-2-4-8(6)10(13)14/h2-4H,5H2,1H3,(H,11,12)

InChIKey

LWIOFILTAJJDLA-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=CC=CC([N+]([O-])=O)=C1C

CAS DataBase Reference

23876-15-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

2-Methyl-3-nitrophenylacetic Acid Usage And Synthesis

Chemical Properties

Yellow solid

Uses

2-Methyl-3-nitrophenylacetic Acid is a pharmaceutical intermediate compound used in the preparation of ropinirole hydrochloride, an oral non-ergot alkaloid dopamine agonist used to treat the symptoms of Parkinson's disease and restless legs syndrome.

Synthesis

General procedure for the synthesis of 2-methyl-3-nitrophenylacetic acid from 2-methyl-3-nitrobenzonitrile: To a solution of 2-methyl-3-nitrophenylacetonitrile (500 mg, 2.8 mmol) in ethanol (30 mL) was added a 20% w/v aqueous KOH solution (30 mL). The reaction mixture was heated to reflux for 18 hours. After completion of the reaction, it was cooled to room temperature and extracted with dichloromethane (50 mL) to separate the aqueous layer. The aqueous layer was acidified to pH 2 with 2N HCl aqueous solution and subsequently extracted with ethyl acetate (50 mL) and dichloromethane (50 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure to afford the light brown solid product 2-methyl-3-nitrophenylacetic acid (470 mg, 86% yield). The product was characterized by 1H NMR (400 MHz, CD3OD) with chemical shifts δ (ppm) of 7.66 (d, 1H), 7.50 (d, 1H), 7.34 (t, 1H), 3.79 (s, 2H), 2.37 (s, 3H).

References

[1] Journal of Medicinal Chemistry, 1985, vol. 28, # 10, p. 1533 - 1536
[2] Patent: US2005/267096, 2005, A1. Location in patent: Page/Page column 29
[3] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 14, p. 1935 - 1939
[4] Journal of the Chemical Society. Perkin transactions 1, 1969, vol. 14, p. 1935 - 1939
[5] Patent: WO2006/123356, 2006, A1. Location in patent: Page/Page column 22; 23

2-Methyl-3-nitrophenylacetic Acid(23876-15-5)Related Product Information

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