4-(Methylamino)benzoic acid → Cis-4-(methylamino)cyclohexanecarboxylic acid
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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customThe insolubles were removed by filtration
- customThe slurry from partial removal of water under reduced pressure
- additionwas diluted with 300 ml of N,N-dimethylformamide
- temperaturechilled
- filtrationThe precipitated solid was filtered
- washwashed with several portions of cold acetone
- customdried
Sources & evidence
- ORD record
- ord-1abd61c4c37a44ee91023e6cb152d183
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04548929
Reaction notes
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