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

HRID 11562

反応式

HRID 11562 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f62c3c18b80740c0b6b9fd0839671267
出典データセット
uspto-grants-2006_08
特許番号
US07098236B2

関連ノート

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