Stannous Chloride → N~1~-Cyclohexylbenzene-1,2-diamine

HRID 220815Notes

Reaction equation

HRID 220815 reaction equation
[CH:1]1([NH: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.[Sn](Cl)Cl>CO>[CH:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 3101179N-cyclohexyl-2-nitroaniline

Product 1

HCID 1517328N~1~-Cyclohexylbenzene-1,2-diamineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexyl-(2-nitro-phenyl)-amine from Example E26.1 (3.0 g, 13.6 mmol) was dissolved in methanol (100 ml) and tin (II) chloride (12.9 g, 68.1 mmol) was added. The mixture was stirred for 20 h at room temperature then heated at reflux for 18 h and concentrated in vacuo. The residue was placed in EtOAC (100 ml), cooled down to 0° C. and pH was adjusted to 14 with conc. NH3. The precipitate was filtered off and washed with EtOAc. The filtrate was washed with 2M NH3, water then brine, dried and concentrated in vacuo to yield the title compound (2.25 g, 86%).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. temperaturecooled down to 0° C.
  5. filtrationThe precipitate was filtered off
  6. washwashed with EtOAc
  7. washThe filtrate was washed with 2M NH3, water
  8. dry with materialbrine, dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f7589b840c24eaab392de25166d05a7
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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