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

HRID 11562

Reaction equation

[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

Participants

Conditions

Temperature: 35 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f62c3c18b80740c0b6b9fd0839671267
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098236B2

Linked notes

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