189816-05-5

189816-05-5 - Names and Identifiers

Name	Quinoline,4-chloro-7-methoxy-2-phenyl-
Synonyms	4-Chloro-7-methoxy-2-phenylquinoline 4-chloro-7-methoxy-2-phenyl-Quinoline Quinoline,4-chloro-7-methoxy-2-phenyl- Quinoline, 4-chloro-7-methoxy-2-phenyl-
CAS	189816-05-5
InChI	InChI=1/C16H12ClNO/c1-19-12-7-8-13-14(17)10-15(18-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H3

189816-05-5 - Physico-chemical Properties

Molecular Formula	C16H12ClNO
Molar Mass	269.73
Density	1.237
Melting Point	96-99°C
Boling Point	414.3±40.0 °C(Predicted)
Flash Point	204.353°C
Vapor Presure	0mmHg at 25°C
pKa	3.46±0.27(Predicted)
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C
Refractive Index	1.638

189816-05-5 - Reference Information

Application

4-chloro-7-methoxy-2-phenylquinoline is an organic intermediate that can be made of 3-methoxyaniline and benzoylacetate Ethyl acetate is prepared in two steps as starting materials, which can be used in laboratory research and development processes and chemical production processes.

Preparation

Step 1: Add HCl (dioxane solution with a concentration of 4.0N, 12.2mL,48.8mmol) to a solution of 3-methoxyaniline (300g,2.44mol) and benzoyl ethyl acetate (234.2g,1.22mol) in toluene (2.0L). The resulting solution was refluxed for 6.5 hours using a Dean-Stark device (about 56mL of aqueous solution was collected). The mixture was cooled to room temperature, divided several times with HCl aqueous solution (10%,3 × 500mL), NaOH aqueous solution (1.0N,2 × 200mL) and water (3 × 200mL), the organic layer was dried (MgSO4), filtered and vacuum concentrated to obtain oily residue (329.5g). The crude product was heated in an oil bath (280°C) for 80 minutes (collecting about 85mL of liquid) using a Dean-Stark device. The reaction mixture was cooled to room temperature, the solid residue was ground with CH2Cl2(400mL), the resulting suspension was filtered and the cake was washed with CH2Cl2(2 × 150mL). The resulting solid was vacuum-dried (50°C; 1 Torr; 1 day) to give an analytically pure product, which was a light brown solid (60.7g, total 20%). Step 2: The product of Step 1 (21.7g,86.4mmol) is suspended in POCl3(240mL). The suspension was refluxed for 2 hours. After removing POCl3 in vacuum, the residue was divided between ethyl acetate (1L) and cold aqueous NaOH solution (prepared from 200mL 1.0N NaOH and 20mL 10.0N NaOH) and stirred for 15 minutes. The organic layer was washed with water (2 × 200mL) and brine (200mL), dried (MgSO4) and concentrated in vacuum to obtain the desired product (21.0g,90%), which is a light brown solid.

Last Update：2024-04-09 21:00:56