| Identification | Back Directory | [Name]
4-Chloro-7-methoxy-2-phenylquinoline | [CAS]
189816-05-5 | [Synonyms]
4-Chloro-7-methoxy-2-phenylquinoline
Quinoline, 4-chloro-7-methoxy-2-phenyl-
4-Chloro-7-methoxy-2-phenylquinoline ISO 9001：2015 REACH | [Molecular Formula]
C16H12ClNO | [MDL Number]
MFCD11042872 | [MOL File]
189816-05-5.mol | [Molecular Weight]
269.73 |
| Questions And Answer | Back Directory | [Synthesis]
Step 1: To a solution of 3-methoxyaniline (300 g, 2.44 mol) and ethyl benzoyl (234.2 g, 1.22 mol) in toluene (2.0 L), HCl (4.0 N dioxane solution, 12.2 mL, 48.8 mmol) was added. The resulting solution was refluxed for 6.5 h using a Dean-Stark apparatus (approximately 56 mL of aqueous solution was collected). The mixture was cooled to room temperature and partitioned multiple times with HCl aqueous solution (10%, 3×500 mL), NaOH aqueous solution (1.0 N, 2×200 mL), and water (3×200 mL). The organic layer was dried (MgSO₄), filtered, and concentrated under vacuum to give an oily residue (329.5 g). The crude product was heated in an oil bath (280 °C) for 80 minutes using a Dean-Stark apparatus (collecting approximately 85 mL of liquid). The reaction mixture was cooled to room temperature, and the solid residue was ground with CH₂Cl₂ (400 mL). The resulting suspension was filtered, and the filter cake was washed with CH₂Cl₂ (2×150 mL). The resulting solid was dried under vacuum (50 °C; 1 Torr; 1 day) to give an analytically pure product, which was a light brown solid (60.7 g, total 20%). Step 2: The product from Step 1 (21.7 g, 86.4 mmol) was suspended in POCl₃ (240 mL). The suspension was refluxed for 2 hours. After removing the POCl₃ under vacuum, the residue was partitioned between ethyl acetate (1 L) and cold NaOH aqueous solution (prepared from 200 mL of 1.0 N NaOH and 20 mL of 10.0 N NaOH) and stirred for 15 minutes. The organic layer was washed with water (2 × 200 mL) and brine (200 mL), dried (MgSO₄), and concentrated under vacuum to obtain the desired product (21.0 g, 90%), which was a light brown solid. | [Application]
4-Chloro-7-methoxy-2-phenylquinoline is an organic intermediate that can be prepared in two steps from 3-methoxyaniline and ethyl benzoyl ethyl acetate as starting materials. It can be used in laboratory research and development processes and chemical production processes. |
| Chemical Properties | Back Directory | [Melting point ]
96-99°C | [Boiling point ]
414.3±40.0 °C(Predicted) | [density ]
1.237 | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
3.46±0.27(Predicted) |
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| Company Name: |
SynAsst Chemical.
|
| Telephone: |
021-60343070 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList15848/0_EN.htm |
| Company Name: |
DKMbiochem.Co. Ltd
|
| Telephone: |
15901859516 |
| Website: |
http://www.dkmbiochem.com/ |
|