2-(4-Nitrophenyl)propionic acid → 4-Aminohydratropic acid

HRID 2173341Notes

Reaction equation

HRID 2173341 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 892442-(4-Nitrophenyl)propionic acid

Product 1

HCID 430264-Aminohydratropic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-nitrophenyl) propionic acid (5 g, 25.6 mmol) was dissolved in ethyl acetate (50 ml) and palladium on carbon (1 g, 9.40 mmol) was added then stirred under hydrogen balloon overnight. The product precipitated out. Added methanol to dissolved product then filtered off the palladium catalyst. The filtrate was concentrated and the residue was triturated with ethyl acetate to yield 2-(4-aminophenyl) propionic acid. LC-MS (IE, m/z): 166 [M+1]+;

Workup

  1. customThe product precipitated out
  2. dissolutionAdded methanol to dissolved product
  3. filtrationthen filtered off the palladium catalyst
  4. concentrationThe filtrate was concentrated
  5. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-c7a85b8189814817adc6352fb9575725
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…