| Identification | More | [Name]
Methyl 2-amino-3-nitrobenzoate | [CAS]
57113-91-4 | [Synonyms]
2-AMINO-3-NITROBENZOIC ACID METHYL ESTER
METHYL 2-AMINO-3-NITROBENZOATE
RARECHEM AH CK 0023
Methyl 3-nitroanthranilate
Methyl 2-amino-3-nitrobenzoate 95%
Benzoic acid, 2-amino-3-nitro-, methyl ester
2-AMINO-3-NITRO-BENZOIC ACID METHYL ESTER >98% | [EINECS(EC#)]
671-056-7 | [Molecular Formula]
C8H8N2O4 | [MDL Number]
MFCD02093531 | [Molecular Weight]
196.16 | [MOL File]
57113-91-4.mol |
| Chemical Properties | Back Directory | [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 | [form ]
Solid | [pka]
-2.80±0.25(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [Hazard Note ]
Irritant | [HS Code ]
2916399090 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
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 |
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