HCID 19754698, compound → HCID 19754672, compound

HRID 1588776Notes

Reaction equation

HRID 1588776 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.[Fe]>[C:1]1(=[CH: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]1

Participants

4

Reactant 1

HCID 19754698HCID 19754698, compound

Product 1

HCID 19754672HCID 19754672, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To 1-(cyclohexylidenemethyl)-2-nitrobenzene (1.6 g) in glacial acetic acid (50 mL), at 85° C., was added iron powder (2.07 g). The mixture was refluxed for 15 min. The mixture was cooled and filtered through clay. The filtrate was partitioned between EtOAc and ice water. The ethyl acetate layer was washed well with a saturated NaHCO3 solution, dried (MgSO4), and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexanes to give 2-(cyclohexylidenemethyl)aniline.

Workup

  1. temperatureThe mixture was refluxed for 15 min
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through clay
  4. customThe filtrate was partitioned between EtOAc and ice water
  5. washThe ethyl acetate layer was washed well with a saturated NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-c113d66ae96c4a12a9ca290cbbd3e968
Source dataset
uspto-grants-1993_06
Patent number
US05223526

Reaction notes

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