| 86% |
In toluene for 1h; Heating; |
|
| 63% |
at 110℃; for 4h; |
4.2.1. Preparation of 2-[(3-Chloro-phenylamino)-methylene]-malonic acid diethyl ester29 (2)
A suspension of 3-Chloro-phenylamine (1) 50 g (0.391 mol) in diethyl ethoxymethylenemalonate 119 mL (0.587 mol) was heated at 110 °C for 4 h. The reaction mixture was cooled to room temperature, the solid formed was taken in hexane (10 vol), stirred for 15 min and filtered to get compound 2 as a pale yellow solid. The isolated compound was taken for next step without further purification. Yield; 70 g (63 %) |
| 60% |
at 110℃; for 4h; |
|
|
at 165℃; for 1.5h; |
|
|
at 115 - 120℃; 30-60 min; Yield given; |
|
|
at 110 - 115℃; for 2h; |
|
|
In toluene Heating; |
|
|
With pyridine In toluene for 2h; Heating; |
|
|
In ethanol Heating; |
|
|
at 20 - 130℃; |
|
|
In ethanol at 130℃; for 3h; |
|
|
In ethanol Reflux; |
|
|
at 125 - 130℃; for 2h; |
|
|
at 125 - 130℃; for 2h; |
General methods for the synthesis of substituted-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester 4
General procedure: Substituted aniline 1 (0.01 mol) and diethylethoxy methylene malonate 2 (0.01 mol) weremixed and heated at 125-130 0C for 2 h. Ethanolwas evaporated off from the resulting mixture ofethyl anilinomethylene malonate 3. The crude solidwas filtered on sintered funnel, dried and recrystallized from n-hexane. The malonate 3 (0.01mol) was refluxed with diphenylether (50 mL) for 1h to give 1,4-dihydro-4-oxoquinoline-3-carboxylicacid ethyl ester 4. After 1 h the solution was cooledand the resulting precipitate was filtered off, washedwith n-hexane, and dried. The solid wasrecrystallized from DMF to give substituted-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethylester 4. |
|
at 125 - 130℃; for 3h; |
4.1.4. Preparation of 1,4-dihydro-4-oxo-quinoline-3-carbohydrazide derivatives 10a,b
General procedure: Substituted aniline 7a,b (0.01mol) and diethyl ethoxy methylene malonate (0.01mol) were mixed and heated at 125-130°C for 3h. Ethanol was evaporated off from the resulting mixture of ethyl anilinomethylene malonate. The crude solid was filtered on sintered funnel, dried. The malonate 8a,b (0.01mol) was refluxed with diphenylether (50mL) for 2h to give 1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester 9a,b. After 1h the solution was cooled and the resulting precipitate was filtered off and dried. Substituted-1,4-dihydro-4-oxoquinoline- 3-carboxylic acid ethyl ester 9a,b (0.01mol) was refluxed for 12h with hydrazine hydrate (0.01mol) in absolute ethanol (9mL) to give substituted-4-oxo-1,4 dihydroquinoline-3-carbohydrazide 10a,b. The excess solvent was evaporated off and the resulting mixture was poured into crushed ice. The solid separated was filter on sintered funnel, washed with water and dried. The physical properties and spectral data of 10a,b were being identical with those were reported [61]. |
|
at 100℃; |
|
|
In ethanol at 130℃; for 0.166667h; Microwave irradiation; |
|
|
at 110℃; for 4h; |
Preparation of 2-[(3-Chloro-phenylamino)-methylene]-malonic acid diethyl ester (Int-2):
A suspension of 3-Chloro-phenylamine (Int-l) 50 g (0.391 mol) in diethyl ethoxymethylene malonate 119 mL (0.587 mol) was heated tol 10 °C for 4 h. The reaction mixture was cooled to room temperature, the solid thus formed was taken in hexane (10 vol), stirred for 15 min and filtered to get compound 2 as a Pale yellow solid. The isolated compound was taken for next step without further purification. Yield: 70 g (63 %) |
|
In ethanol for 3h; Reflux; Inert atmosphere; |
|
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