| Identification | Back Directory | [Name]
2-Amino-3,4-dichlorobenzoicacid | [CAS]
20776-62-9 | [Synonyms]
Benzoic acid, 2-amino-3,4-dichloro- | [Molecular Formula]
C7H5Cl2NO2 | [MDL Number]
MFCD00078315 | [MOL File]
20776-62-9.mol | [Molecular Weight]
206.03 |
| Chemical Properties | Back Directory | [Melting point ]
237-238 °C | [Boiling point ]
356.2±42.0 °C(Predicted) | [density ]
1.607±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
4.34±0.10(Predicted) | [Appearance]
Off-white to light yellow Solid |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 2-amino-3,4-dichlorobenzoic acid from 6,7-dichloroindole-2,3-dione: 6,7-dichloroindole-2,3-dione (1 g, 4.6 mmol) was added to an aqueous (10.5 mL) suspension of potassium hydroxide (370 mg, 6.6 mmol) and potassium chloride (920 mg, 12.3 mmol) cooled to 0 °C . Subsequently, a 30 wt% aqueous hydrogen peroxide solution (1.1 mL, 35 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 30 min, then ethyl acetate (4.0 mL) was added. The resulting mixture was washed sequentially with water, the organic layer was separated and dried over anhydrous sodium sulfate. Decarboxylation product (910 mg, 95% yield) was obtained after concentration under reduced pressure. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 13.16 (s, 1H), 7.73 (d, J = 8.6 Hz, 1H), 7.11 (s, 2H), 6.81 (d, J = 8.6 Hz, 1H). | [References]
[1] Patent: WO2016/176449, 2016, A1. Location in patent: Page/Page column 89
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[3] Journal of the American Chemical Society, 1956, vol. 78, p. 1251,1254
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 217 - 222 |
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