ChemicalBook CAS DataBase List ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE

ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE synthesis

5synthesis methods

Product Name:ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE
CAS Number:248282-10-2
Molecular formula:C13H12ClNO4
Molecular Weight:281.69

118-48-9 Synthesis

118-48-9
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74-88-4
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ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE

248282-10-2
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Yield:248282-10-2 74%

Reaction Conditions:

with hydrogenchloride in methanol;N,N-dimethyl acetamide;water;

Steps:

2 1.2Dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester

The anhydride (5 g, 0.025 mol) was dissolved in 50 ml of N,N-dimethylacetamide and cooled to 0° C. Sodium hydride (75%) (0.94 g, 0.028 mol) and then methyl iodide (1.89 ml, 0.030 mol) was added at a rate to keep the temperature below 5° C. The reaction mixture was stirred at room temperature for 5 hours. The remaining methyl iodide was removed uuder vacuum. Sodium hydride (0.94 g, 0.028 mol) was added together with diethyl malonate (4.5 g, 0.028 mol). The mixture was heated at 85° C. for 5 hours. After cooling to room temperature, 50 ml of methanol and 50 ml of 1 M hydrochloric acid and subsequently 250 ml of water were added. An emulsion was formed which crystallized on standing in a refrigerator for 72 hours. The crystalline mass was collected by filtration, washed with water, water/methanol (1:1) and heptane and dried to afford the title compound (6.3 g), yield 74%. 1H NMR (CDCl₃) δ 1.46 (3H, t), 3.63 (3H, s), 4.49 (2H, q), 7.23 (1H, d), 7,27 (1H, d), 7.49 (1H, t), 15.0 (1H, s).

References:

US6133285,2000,A

40707-01-5 Synthesis