(3-Nitrophenoxy)acetic acid → (3-Aminophenoxy)acetic acid

HRID 1809144Notes

Reaction equation

HRID 1809144 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([OH:11])=[O:10])([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 74656(3-Nitrophenoxy)acetic acid

Product 1

HCID 235515(3-Aminophenoxy)acetic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2 L pressure vessel was added 3-nitrophenoxyacetic acid 1 (21.7 g, 110 mmol, 1.0 eq.) and methanol (600 mL). The resulting solution was purged with N2 for 5 min. 10% Pd/C (900 mg) was added to the solution and the vessel was placed on a Parr hydrogenator at 50 psi for 3 h. After removal from the Parr apparatus, the reaction mixture was gray in color, indicating the precipitation of product. DMF (400 mL) was added and was stirred until it was evident that the precipitated product had dissolved in the solvent phase. The Pd/C was removed by filtration and the filtrate was concentrated under high vacuum to yield a dark brown solid (14 g, 76%). LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 168.0 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 7.93 (s, 1H), 6.86 (t, 1H), 6.14-5.99 (m, 3H), 4.50 (s, 2H) ppm.

Workup

  1. customThe resulting solution was purged with N2 for 5 min
  2. addition10% Pd/C (900 mg) was added to the solution
  3. customAfter removal from the Parr apparatus
  4. customthe precipitation of product
  5. additionDMF (400 mL) was added
  6. dissolutionhad dissolved in the solvent phase
  7. customThe Pd/C was removed by filtration
  8. concentrationthe filtrate was concentrated under high vacuum

Sources & evidence

ORD record
ord-4ca9a24a55a246f5ba16efe69334bd1e
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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