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

HRID 252013

反応式

HRID 252013 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒2 回HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-14f852d1d4f649db8f9598f649336091
出典データセット
uspto-grants-2011_01
特許番号
US07867949B2

関連ノート

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