HCID 2769565, compound → HCID 68780079, compound

HRID 2266492Notes

Reaction equation

HRID 2266492 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]([F:30])=[CH:26][CH:25]=1)[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:20]([CH3:21])=[C:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[C:18](=[O:17])[NH:13]2.[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:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[C:20]([CH3:21])[NH:13]2

Participants

5

Reactant 2

HCID 2769565HCID 2769565, compoundHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetate

Product 2

HCID 68780079HCID 68780079, compoundHCID 68787407HCID 68787407, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (1.5 g), 2-(4-fluorobenzyl)-3-oxobutyric acid ethyl ester (1.7 g) and polyphosphoric acid (15 g) was heated at 100° C. for 3 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 then 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 (3:7 by volume) to afford [8-chloro-3-(4-fluorobenzyl)-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic acid methyl ester as a yellow-brown solid, 0.13 g and [8-chloro-3-(4-fluorobenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester as a brown oil, 0.21 g.

Workup

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

Sources & evidence

ORD record
ord-fdbfb1306df54530816d303ce07253fb
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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