4-(Methylamino)benzoic acid → Cis-4-(methylamino)cyclohexanecarboxylic acid

HRID 2295293

Reaction equation

HRID 2295293 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[H][H]>[Rh].O>[CH3:1][NH:2][CH:3]1[CH2:11][CH2:10][CH:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 663454-(Methylamino)benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 429561Cis-4-(methylamino)cyclohexanecarboxylic acidYield 75%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent

Procedure

A slurry of 33.0 g (0.218 m) of 4-(methylamino)benzoic acid and 4.0 g of 5% rhodium on alumina catalyst in 350 ml of water was shaken under 1500 psig of hydrogen for 24 hours. The insolubles were removed by filtration. The slurry from partial removal of water under reduced pressure was diluted with 300 ml of N,N-dimethylformamide and chilled. The precipitated solid was filtered, washed with several portions of cold acetone, and dried to yield 23 g (75%) of 4-(methylamino)cyclohexanecarboxylic acid.

Workup

  1. customThe insolubles were removed by filtration
  2. customThe slurry from partial removal of water under reduced pressure
  3. additionwas diluted with 300 ml of N,N-dimethylformamide
  4. temperaturechilled
  5. filtrationThe precipitated solid was filtered
  6. washwashed with several portions of cold acetone
  7. customdried

Sources & evidence

ORD record
ord-58d2685837484985a77bef64d1f51f42
Source dataset
uspto-grants-1984_01
Patent number
US04424213

Linked notes

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