Acetic Acid → 4-Aminobenzoic Acid

HRID 2270153Notes

Reaction equation

HRID 2270153 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11]C=C[C:5]=1[C:6](O)=O)([O-])=O.[H][H].[C:15]([OH:18])(=[O:17])[CH3:16]>C(O)C.[Pd]>[CH:6]1[C:16]([C:15]([OH:18])=[O:17])=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 110872-Nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 9784-Aminobenzoic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (1.98 g) was added to a 450 mL hydrogenation flask, and the flask was flushed with N2. A solution of nitro benzoic acid 1 (21.9 g, 118.3 mmol) in 140 mL ethanol and acetic acid (1 mL) were added to the flask. Hydrogenation was conducted at 15 psi in a carefully controlled manner, wherein after the pressure of H2 drops to zero, the shaking of the flask was continued for a couple of minutes before re-pressurizing. After the hydrogen uptake ceased, the pressure was raised to 40 psi, and continued shaking for an additional 30 minutes to insure completion of the reduction. The catalyst was filtered through Celite, and solvent was removed in vacuo to afford amino benzoic acid 2 as an off-white solid.

Workup

  1. customthe flask was flushed with N2
  2. waitwas continued for a couple of minutes before re-pressurizing
  3. temperaturethe pressure was raised to 40 psi
  4. stirringcontinued shaking for an additional 30 minutes
  5. filtrationThe catalyst was filtered through Celite, and solvent
  6. customwas removed in vacuo

Sources & evidence

ORD record
ord-bea0060e293d4fac894b0d90a01bd0c0
Source dataset
uspto-grants-2001_12
Patent number
US06331570B1

Reaction notes

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