Acetic Acid → 2-(Cyclohexylmethyl)aniline
Reaction equation
[C:1]1(=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C>[Pd].C(O)C>[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(Cyclohexylidenemethyl)-2-nitrobenzene (3.45 g), prepared as above, glacial acetic acid (30 mL), ethanol (50 mL), and a catalytic amount of 10%Pd/C were shaken on a Parr Hydrogenator under a atmosphere of hydrogen at 23° C. for 24 h. The mixture was filtered through clay and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 10% EtOAc/hexanes to give 2-(cyclohexylmethyl)aniline.
Workup
- filtrationThe mixture was filtered through clay
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel eluting with 10% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-c3172802712b4a0f986e663d81430144
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223526
Reaction notes
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