4-(4-Acetamidophenyl)-4-oxobutanoic acid → 4-(4-Aminophenyl)-4-oxobutanoic acid

HRID 1264089Notes

Reaction equation

HRID 1264089 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:7][CH:6]=1)(=O)C>Cl>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 2323374-(4-Acetamidophenyl)-4-oxobutanoic acid

Product 1

HCID 2432904-(4-Aminophenyl)-4-oxobutanoic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 4-(4-acetylamino-phenyl)-4-oxo-butyric acid (9.84 g, 0.0418 mol) in 1.0 M hydrocloric acid (125 mL) was heated on a steam bath for 1.5 hours, gravity filtered hot, and the filtrate allowed to cool. To the stirred solution was added 50% wt/wt sodium hydroxide (9.7 g) dropwise until pH equaled 3 to 4. The resulting precipitate was filtered, and the filtercake was washed with very dilute hydrochloric acid. The procedure was repeated on the solids with fresh 1.0 M hydrochloric acid (100 mL) to give 7.00 g of 4-(4-amino-phenyl)-4-oxo-butyric acid as a tan solid.

Workup

  1. temperaturewas heated on a steam bath for 1.5 hours
  2. filtrationgravity filtered hot
  3. temperatureto cool
  4. additionTo the stirred solution was added 50% wt/wt sodium hydroxide (9.7 g) dropwise until pH
  5. filtrationThe resulting precipitate was filtered
  6. washthe filtercake was washed with very dilute hydrochloric acid

Sources & evidence

ORD record
ord-55b1dda91983440fb40f5814f2b289b3
Source dataset
uspto-grants-2003_04
Patent number
US06541521B1

Reaction notes

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