ChemicalBook CAS DataBase List 3-METHYL-2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID

3-METHYL-2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID synthesis

4synthesis methods

Product Name:3-METHYL-2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID
CAS Number:43071-45-0
Molecular formula:C17H13NO2
Molecular Weight:263.29

91-56-5 Synthesis

91-56-5
457 suppliers
$5.00/25g

93-55-0
7 suppliers
$15.00/25g

3-METHYL-2-PHENYL-QUINOLINE-4-CARBOXYLIC ACID

43071-45-0
41 suppliers
$97.00/100mg

Yield:43071-45-0 85%

Reaction Conditions:

with hydrogenchloride;potassium hydroxide in ethanol;water;

Steps:

A Method A

Method A Carboxylic acid precursors of exemplary compounds disclosed herein, see Table 1 hereafter, were made in a manner analogous to the following method. 3-methyl-2-phenyl-4-quinolinecarboxylic Acid. A solution of isatin (5.00 g, 34.0 mmol), propiophenone (5.47 g, 5.43 mL, 40.8 mmol), and potassium hydroxide pellets (6.73 g, 102 mmol) in ethanol (40 mL) was stirred at reflux for 23 h. After cooling, the solvent was removed in vacuo to give a brown residue. The residue was dissolved in water (75 mL) and washed with diethyl ether (4*100 mL). The aqueous layer was cooled by the addition of ice (~50 g) and acidified to pH~1 via dropwise addition of concentrated HCl with stirring. A solid precipitate was collected by filtration, washed with water and dried to provide the title compound as a yellowish-tan solid (7.59 g, 85%), which was used without further purification. MS (API+): M+1: 264 (45%), 220 (100); %); ¹H NMR (300 MHz, DMSO-d₆) d 2.39 (s, 3H), 7.49-7.57 (m, 3H), 7.59-7.72 (m, 3H), 7.76-7.84 (m, 2H), 8.06 (d, J=8.5 Hz, 1H), 14.20 (v br s, 1H, exchangeable).

References:

US2004/53964,2004,A1