(4-Nitrophenyl)acetic acid → 1-(4-Morpholinyl)-2-(4-nitrophenyl)ethanone

HRID 2219187

반응식

HRID 2219187 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:14]1([C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8083MorpholineHCID 516892Sodium Bicarbonate

생성물 1

HCID 51701651-(4-Morpholinyl)-2-(4-nitrophenyl)ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
35 °C

실험 절차

A room temperature solution of 1.8839 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (5 mL) is treated with 1.8069 gms. 1′,1′-carbonyl-diimidizole. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 1.0 mL morpholine. The reaction is heated overnight at 35° C. The reaction is then allowed to cool to room temperature, and is made basic with the addition of saturated aqueous sodium bicarbonate. The resulting mixture is extracted with ethyl acetate. The aqueous layer is re-extracted four more times with ethyl acetate. The combined organics are evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 60% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-morpholin-4-yl-2-(4-nitro-phenyl)-ethanone is isolated as a white solid in the amount of 1.4009 gms.

후처리

  1. customA room temperature solution of 1.8839 gms
  2. temperatureto cool to room temperature
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. extractionThe aqueous layer is re-extracted four more times with ethyl acetate
  5. customThe combined organics are evaporated to dryness in vacuo
  6. customThe crude product residue is then chromatographed by flash silica gel chromatography
  7. customevaporation of solvent

출처 및 근거

ORD 기록
ord-2fbf54534b02460899091b2826bc383b
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414054B2

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