Methyl 2-amino-3-nitrobenzoate Chemical Properties

Melting point:

97-98°C

Boiling point:

340.1±22.0 °C(Predicted)

Density 

1.386±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Ethyl Acetate

pka

-2.80±0.25(Predicted)

form 

Solid

color 

Yellow

InChI

InChI=1S/C8H8N2O4/c1-14-8(11)5-3-2-4-6(7(5)9)10(12)13/h2-4H,9H2,1H3

InChIKey

HDCLJQZLTMJECA-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC([N+]([O-])=O)=C1N

CAS DataBase Reference

57113-91-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2916399090

Methyl 2-amino-3-nitrobenzoate Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

Methyl 2-amino-3-nitrobenzoate is used as an intermediate in the preparation of Candesartan.

Synthesis

2-Amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) was dissolved in methanol (40 mL) followed by the addition of concentrated sulfuric acid (0.50 mL). The reaction mixture was heated to reflux for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with saturated aqueous sodium bicarbonate to about 9. The mixture was concentrated under reduced pressure to about 10 mL, water (20 mL) was added, and the mixture was extracted with ethyl acetate (10 mL x 3 times). The organic layers were combined and dried with anhydrous magnesium sulfate. The organic layers were concentrated under reduced pressure and the resulting crystals were dried to give methyl 2-amino-3-nitrobenzoate. The product was structurally confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H-NMR). Yield: 661.4 mg (61%). 1H-NMR (270 MHz, CDCl3): δ 8.50 (br, s), 8.37 (1H, dd, J = 8.6, 1.4 Hz), 8.23 (1H, dd, J = 7.6, 1.4 Hz), 6.65 (1H, dd, J = 8.6, 7.6 Hz), 3.92 (3H, s ) ppm.

References

[1] Patent: EP1452528, 2004, A1. Location in patent: Page 21-22
[2] Patent: EP1502916, 2005, A1. Location in patent: Page 435
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[5] Patent: WO2007/100295, 2007, A1. Location in patent: Page/Page column 253

Methyl 2-amino-3-nitrobenzoate(57113-91-4)Related Product Information

• Kresoxim-methyl
• Methyl 2-bromobenzoate
• 2-Amino-3-nitrophenol
• 2-Amino-3-nitrobenzoic acid
• Methyl acetate
• 6-Aminocaproic acid
• Trimethoxymethane
• Glycine
• Methylparaben
• Methyl anthranilate
• METHYL THIOPHENE-2-CARBOXYLATE
• Methyl formate
• Methyl benzoate
• Methyl acrylate
• 4-Amino-3-nitrobenzoic acid
• Bensulfuron methyl
• Thiophanate-methyl
• Methyl