2-Chloro-N-(4-methoxyphenyl)acetamide → 5-Hydroxyoxindole

HRID 1865188Notes

Reaction equation

HRID 1865188 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3]>>[OH:12][C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[NH:5][C:3](=[O:4])[CH2:2]2

Participants

3

Reactant 2

HCID 311232-Chloro-N-(4-methoxyphenyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 769555-Hydroxyoxindole

Conditions

Temperature
240 °C

Procedure

2-chloro-N-(4-methoxyphenyl)-acetamide (10 g) and Anhydrous aluminum trichloride (17 g) was heated to 120° C. for 15 minutes and then heated to 240° C. for 1 hour. The reaction was cooled to room temperature and quenched with ice water and Concentrate hydrochloride acid, and extracted with ethyl acetate (5×). Organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude solid was flash chromatography (silica, ethyl acetate) to give product.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with ice water
  3. concentrationConcentrate hydrochloride acid
  4. extractionextracted with ethyl acetate (5×)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give product

Sources & evidence

ORD record
ord-e4bf43d92a1e4e518bca51260ff72643
Source dataset
uspto-grants-2009_12
Patent number
US07626031B2

Reaction notes

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