ChemicalBook CAS DataBase List 6-METHOXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

6-METHOXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis

5synthesis methods

Product Name:6-METHOXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS Number:26660-48-0
Molecular formula:C13H13NO3
Molecular Weight:231.25

ethyl 4-chloro-6-methoxy-quinoline-3-carboxylate

22931-71-1
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6-METHOXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

26660-48-0
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Yield:26660-48-0 9.18 g (51.5%)

Reaction Conditions:

with triethylamine;palladium in ethanol;dichloromethane;cyclohexane;

Steps:

28 Preparation of 3-Ethoxycarbonyl-6-methoxyquinoline

EXAMPLE 28 Preparation of 3-Ethoxycarbonyl-6-methoxyquinoline A mixture of 20 g (75.8 mmol) of 3-ethoxycarbonyl-4-chloro-6-methoxyquinoline, 1.5 g of 10% palladium on carbon catalyst, 20 mL of triethylamine and 300 mL of ethanol was shaken under a hydrogen atmosphere (30 psi) at room temperature overnight. The catalyst was removed by filtration and the filtrate was evaporated. The residue was dissolved in methylene chloride, washed with aqueous sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and evaporated in vacuo. That residue was suspended in 500 mL of cyclohexane and the resultant suspension was refluxed, then filtered to remove insoluble materials. The filtrate was allowed to stand at room temperature and the crystalline material which formed was collected to give 9.18 g (51.5%) of a pale brown solid having the structural formula: STR99 NMR (CDCl₃) δ 9.25 (1H, d), 8.7 (1H, d), 8.05 (1H, d, J=9 Hz), 7.5 (1H, dd, J=9 Hz, 3 Hz), 7.2 (1H, d, J=3 Hz), 4.45 (2H, q), 3.9 (3H, s), 1.45 (3H, t). IR (KBr) ν 1713, 1620, 1600, 1500, 1240, 1100, 1025 cm^-1.

References:

US4888427,1989,A