ChemicalBook CAS DataBase List 1-methyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid(SALTDATA: FREE)

1-methyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid(SALTDATA: FREE) synthesis

9synthesis methods

Product Name:1-methyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid(SALTDATA: FREE)
CAS Number:67984-94-5
Molecular formula:C11H9NO3
Molecular Weight:203.19

ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate

85870-47-9
54 suppliers
$65.00/50mg

74-88-4
346 suppliers
$15.00/10g

1-methyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid(SALTDATA: FREE)

67984-94-5
22 suppliers
$45.00/50mg

Yield:67984-94-5 350 mg

Reaction Conditions:

Stage #1: 1,2-dihydro-2-oxo-3-quinolinecarboxylic acid,ethyl ester;methyl iodidewith potassium carbonate in N,N-dimethyl-formamide at 20;
Stage #2: with water;sodium hydroxide in N,N-dimethyl-formamide at 20; for 4 h;

Steps:

1.C (C) 1-methyl-2-oxo-1, 2-dihydroquinoline-3-carboxylic acid

Ethyl 2-oxo-1, 2-dihydroquinoline-3-carboxylate (500 mg, 2.3 mmol) , iodomethane (430 μl, 6.9 mmol) , potassium carbonate (636 mg, 4.6 mmol) and DMF (5 ml) were successively added to a reaction flask, and the mixture was stirred at room temperature overnight. Sodium hydroxide aqueous solution (2N, 4 ml) was added dropwise, and the reaction solution was stirred at room temperature for 4 hours. Water (100 ml) was added, and the pH was adjusted to 4 with concentrated hydrochloric acid. The reaction solution was filtered, and the solid was washed with water and dried, to obtain 350 mg of the title product as a white solid. MS (m/z) : 204.1 [M+H]⁺.

References:

WO2021/197276,2021,A1 Location in patent:Page/Page column 56; 57