Ethanol → 3-[(3,5-Dimethylphenyl)amino]propanoic acid

HRID 1107972Notes

Reaction equation

HRID 1107972 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[NH:5][CH2:6]CC#N.[OH-:14].[Na+].[CH2:16]([OH:18])[CH3:17]>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[NH:5][CH2:6][CH2:17][C:16]([OH:14])=[O:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2926323-(3,5-Dimethylanilino)propanenitrile

Product 1

HCID 24348423-[(3,5-Dimethylphenyl)amino]propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

β-(3,5-Dimethylanilino)propionitrile (4.5 g) was dissolved in ethanol (50 ml), and a solution of NaOH (5.1 g) in water (25 ml) was added, which was followed by refluxing for 4 hr. The solvent was evaporated under reduced pressure. 2N Hydrochloric acid was added to adjust the residue acidic, and the mixture was washed with chloroform (100 ml). The aqueous layer was concentrated to about 20 ml and allowed to stand. The precipitated crystals were collected by filtration and dried to give 4.0 g of β-(3,5-dimethylanilino)propionic acid.

Workup

  1. temperatureby refluxing for 4 hr
  2. customThe solvent was evaporated under reduced pressure
  3. addition2N Hydrochloric acid was added
  4. washthe mixture was washed with chloroform (100 ml)
  5. concentrationThe aqueous layer was concentrated to about 20 ml
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-8619bf8f1da2414f91f1f6730bdebda4
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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