Methyl 2-(3-amino-4-chlorophenoxy)acetate → HCID 68782003, compound

HRID 2266517Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.[Cl:15][C:16]1[CH:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=[CH:26][C:17]=1[CH2:18][CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21]>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:20]([CH3:21])=[C:19]([CH2:18][C:17]1[CH:26]=[CH:27][C:28]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:29][C:16]=1[Cl:15])[C:23]([CH3:24])=[N:13]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.35 g), 3-(2-chloro-4-methanesulfonylbenzyl)pentane-2,4-dione (0.5 g) and polyphosphoric acid (5.0 g) was heated at 100° C. for 3.5 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (2:8 to 3:7 by volume) to afford title compound as a pale yellow waxy solid, 0.36 g.

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe combined extracts were washed with water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue purified by column chromatography on silica gel
washeluting with a mixture of ethyl acetate and cyclohexane (2:8 to 3:7 by volume)

Sources & evidence

ORD record: ord-8b9d164d7d1140c6ad3101a9ebb170a1
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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