Hydrochloric Acid → Ethyl 2-(3-Chloro-2-pyridinyl)-5-oxo-3-pyrazolidinecarboxylate

HRID 252013

반응식

HRID 252013 반응식
[Cl:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[O-]CC.[Na+].[C:14](OCC)(=[O:22])/[CH:15]=[CH:16]\[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(O)C.O.C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:8]2[CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][C:14](=[O:22])[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 5561003-Chloro-2-hydrazinylpyridineHCID 2723922Sodium ethoxideHCID 5271566Diethyl Maleate

생성물 1

HCID 22280352Ethyl 2-(3-Chloro-2-pyridinyl)-5-oxo-3-pyrazolidinecarboxylate

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 702Ethanol용매2회HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

To a mixture of 20 g of 3-chloro-2-hydrazinopyridine, 56 ml of sodium ethoxide (a 21% solution in ethanol) and 75 ml of ethanol was added dropwise 27 ml of diethyl maleate. The resulting mixture was heated to reflux for 10 minutes. The reaction mixture was allowed to cool to 65° C., and 15 ml of acetic acid was poured into the mixture. The reaction mixture was allowed to cool to room temperature. After 190 ml of water was poured into the reaction mixture, the mixture was adjusted to pH 2 by an addition of 6N hydrochloric acid and then extracted with methyl tert-butyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the resulting residue, and a solid was collected by filtration to obtain 4.28 g of ethyl 2-(3-chloro-2-pyridinyl)-5-oxo-3-pyrazolidinecarboxylate of the formula:

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 10 minutes
  3. temperatureto cool to room temperature
  4. extractionextracted with methyl tert-butyl ether three times
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionDiethyl ether was added to the resulting residue
  9. filtrationa solid was collected by filtration

출처 및 근거

ORD 기록
ord-14f852d1d4f649db8f9598f649336091
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07867949B2

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