Methyl 2-(3-amino-4-chlorophenoxy)acetate → HCID 68780451, compound

HRID 2266507Notes

Reaction equation

HRID 2266507 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.C([O:17][C:18](=O)[CH:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][C:25]=1[Cl:34])[C:20](=O)[CH3:21])C>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:18](=[O:17])[C:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][C:25]=1[Cl:34])=[C:20]([CH3:21])[NH:13]2

Participants

4

Reactant 2

HCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 687794542-(2-chloro-4-methanesulfonylbenzyl)-3-oxobutyric Acid Ethyl Ester

Product 1

HCID 68780451HCID 68780451, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.85 g), 2-(2-chloro-4-methanesulfonylbenzyl)-3-oxobutyric acid ethyl ester (2.1 g) and polyphosphoric acid (10 g) was heated at 130° C. for 2 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel to afford title compound, 0.35 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-19e91dc69e114470ae8f5c2a46c7ee82
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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