[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy-
[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy-
CAS: 376592-93-7
Molecular Formula: C13H11NO3
[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- - Names and Identifiers
| Name | [1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- |
| Synonyms | EltroMbopag I Eltrombopag Intermediate 2 Eltrombopag olamine Intermediate 1 3-(3-aMino-2-hydroxyphenyl)benzoic acid 3''-AMINO-2''-HYDROXY-BIPHENYL-3-CARBOXYLIC 3'-Amino-2'-Hydroxy-Biphenyl-3-Carboxylic Acid 3''-AMINO-2''-HYDROXY-BIPHENYL-3-CARBOXYLIC ACID 3''-Amino-2''-Hydroxy-Biphenyl-3-Carboxylic Acid 3'-Amino-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid [1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- [1,1'-Biphenyl]-3-carboxylic acid, 3'-aMino-2'-hydroxy- |
| CAS | 376592-93-7 |
| EINECS | 814-404-7 |
[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- - Physico-chemical Properties
| Molecular Formula | C13H11NO3 |
| Molar Mass | 229.23 |
| Density | 1.364 |
| Melting Point | 222 °C(dec.) |
| Boling Point | 474.8±45.0 °C(Predicted) |
| Solubility | DMSO (Slightly), Methanol (Slightly, Heated) |
| Appearance | Solid |
| Color | Pale Yellow to Light Brown |
| pKa | 3.99±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 4.362 ml | 21.812 ml | 43.624 ml |
| 5 mM | 0.872 ml | 4.362 ml | 8.725 ml |
| 10 mM | 0.436 ml | 2.181 ml | 4.362 ml |
| 5 mM | 0.087 ml | 0.436 ml | 0.872 ml |
Last Update：2024-01-02 23:10:35
[1,1'-Biphenyl]-3-carboxylicacid, 3'-amino-2'-hydroxy- - Reference Information
| use | 3 '-amino -2'-hydroxy-[1,1 '-biphenyl]-3-formic acid is often used to synthesize medicines and pesticides Important raw materials or intermediates play an important role in the synthesis of cardiovascular drugs. |
| synthesis method | 3 '-amino -2'-hydroxy-[1,1 '-biphenyl]-3-formic acid synthesis steps are as follows: step 1: stir Na2CO3(424 mg,4 mmol), Pd(OAc)2(22.4 mg,5 mol%), a mixture of PEG 2000(7g) and water (6 mL) was heated to 50°C. Subsequently, 2-bromo-4-chloro-6-nitrophenol (compound lb,508 mg,2 mmol) and 3-carboxyphenylboronic acid (compound 3)(494 mg,3 mmol) were added to the solution and the mixture was heated at 50°C under an inert atmosphere. After 3.5 hours, the reaction mixture was cooled to room temperature, diluted with water (50 mL), and treated with 5% aqueous solution. HCl was adjusted to pH = 2 and extracted with ethyl acetate (3 × 20 mL). The combined ethyl acetate extract was washed with water and salt water (50 mL), dried on anhydrous Na2SO4 and concentrated in vacuum. The crude product was obtained in brown solid form and recrystallized from 60% acetic acid/water. Compound (2b)(340 mg,58%, purity 92%,HPLC method B). Step 2: Dissolve 5 '-chloro -2'-hydroxy -3 '-nitrobiphenyl -3-carboxylic acid (compound 2b)(5.0g) in a mixture of MeOH(300 mL) and Et3N(4.75 mL). Pd/C(0.5g) was added to the solution and the mixture was hydrogenated at room temperature and 10 bar pressure for 21 h. The catalyst is then removed by filtration, the filtrate is concentrated to dry, and the residue is dissolved in water (40 mL). The pH was adjusted to 5.5 by dropping 0.5 M HCl and the resulting suspension was stirred for 30 minutes at room temperature. The suspension was filtered, the collected solids were washed with water (2 × 10 mL) and dried at 50°C/50 mbar to give 3 '-amino -2'-hydroxy-[1,1 '-biphenyl]-3-formic acid. BPCA(3.4g; 86.7%;HPLC purity 97.9%). Fig. 3 '-amino -2'-hydroxy-[1,1 '-biphenyl]-3-formic acid synthesis route |
Last Update：2024-04-09 20:15:17
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