3-Aminobenzoic Acid → 3-Aminocyclohexanecarboxylic acid

HRID 2270819Notes

Reaction equation

HRID 2270819 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[H][H]>C(O)C.[Pd]>[NH2:1][CH:2]1[CH2:10][CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3]1

Participants

5

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 5448873-Aminocyclohexanecarboxylic acidYield 57.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-aminobenzoic acid (66.12 g, 0.48 mol) and 10% palladium-on-carbon (13.2 g) in 30% aqueous ethanol (1200 mL) was placed in a 4 L stainless steel high-pressure reactor and reduced at 50° C. and 500 psi of hydrogen for 30 h. The mixture was filtered through Celite and the filter cake was washed with ethanol. The solvent was evaporated, boiling ethanol (1 L) was added and the mixture was allowed to stand for 8 days at room temperature. The mixture was filtered and the product was washed with ethanol and then dried in a vacuum oven at 50° C., to give 3-aminocyclohexanecarboxylic acid (39.30 g, 57%) as a white solid.

Workup

  1. customwas placed in a 4 L stainless steel high-pressure reactor
  2. customreduced at 50° C.
  3. filtrationThe mixture was filtered through Celite
  4. washthe filter cake was washed with ethanol
  5. customThe solvent was evaporated
  6. additionwas added
  7. filtrationThe mixture was filtered
  8. washthe product was washed with ethanol
  9. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-cde7b4c4a1564676a8b5cb0a8f108e08
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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