Methyl 2-(3-amino-4-chlorophenoxy)acetate → HCID 68783790, compound

HRID 2266526Notes

Reaction equation

HRID 2266526 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.[CH3:15][S:16]([C:19]1[CH:34]=[CH:33][C:22]([CH2:23][CH:24]([C:29](=O)[CH2:30][CH3:31])[C:25](=O)[CH2:26][CH3:27])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>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:25]([CH2:26][CH3:27])=[C:24]([CH2:23][C:22]1[CH:21]=[CH:20][C:19]([S:16]([CH3:15])(=[O:18])=[O:17])=[CH:34][CH:33]=1)[C:29]([CH2:30][CH3:31])=[N:13]2

Participants

4

Reactant 2

HCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetateHCID 68784837HCID 68784837, compound

Product 1

HCID 68783790HCID 68783790, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (0.35 g), 4-(4-methanesulfonylbenzyl)heptane-3,5-dione (0.49 g) and polyphosphoric acid (5.0 g) was heated at 100° 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, eluting with a mixture of dichloromethane and methanol (99.5:0.5 by volume) to afford title compound, 0.20 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
  6. washeluting with a mixture of dichloromethane and methanol (99.5:0.5 by volume)

Sources & evidence

ORD record
ord-cf8df8233742428fbf7b10289a4131d7
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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