Acetic Acid → Ethyl 2-(3,5-dichloropyridin-2-yl)-5-oxopyrazolidine-3-carboxylate

HRID 453076

반응식

HRID 453076 반응식
[O-]CC.[Na+].[Cl:5][C:6]1[C:7]([NH:13][NH2:14])=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1.[C:15](OCC)(=[O:23])/[CH:16]=[CH:17]\[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O)(=O)C>O.C(O)C>[Cl:5][C:6]1[C:7]([N:13]2[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][C:15](=[O:23])[NH:14]2)=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6009663,5-Dichloro-2-hydrazinylpyridineHCID 2723922Sodium ethoxideHCID 5271566Diethyl Maleate

생성물 1

HCID 58158924Ethyl 2-(3,5-dichloropyridin-2-yl)-5-oxopyrazolidine-3-carboxylate수율 47%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

To a 500 mL flask, 300 mL anhydrous ethanol, sodium ethoxide (4.1 g, 61 mmol) and 3,5-dichloro-2-hydrazinylpyridine (10.00 g, 56 mmol) were added. The reaction mixture was heated to reflux for 5 minutes. Diethyl maleate (10.64 g, 61.0 mmol) was added dropwise and heated to reflux for 10 minutes. After being cooled to 65° C., the reaction mixture was neutralized with glacial acetic acid (13 g, 224 mmol) and diluted with 300 mL water. The mixture was cooled down to room temperature and the a precipitate formed. The solid was isolated via filtration, washed with 40% aqueous solution of ethanol (3×50 mL) and dried to give the product (8.00 g) as an orange solid in 47% yield. Melting point: 105-108° C.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 minutes
  3. temperatureheated
  4. temperatureto reflux for 10 minutes
  5. temperatureThe mixture was cooled down to room temperature
  6. customthe a precipitate formed
  7. customThe solid was isolated via filtration
  8. washwashed with 40% aqueous solution of ethanol (3×50 mL)
  9. customdried

출처 및 근거

ORD 기록
ord-72ae61267b1d4b2fa7fd6c36fce7e30f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492409B2

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